CN112312773A - 高纯度甜菊糖苷 - Google Patents
高纯度甜菊糖苷 Download PDFInfo
- Publication number
- CN112312773A CN112312773A CN201880093491.5A CN201880093491A CN112312773A CN 112312773 A CN112312773 A CN 112312773A CN 201880093491 A CN201880093491 A CN 201880093491A CN 112312773 A CN112312773 A CN 112312773A
- Authority
- CN
- China
- Prior art keywords
- rebaudioside
- udp
- stevioside
- glucosyltransferase
- amino acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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Abstract
描述了制备高度纯化的甜菊糖苷的方法,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM。该方法包括使用酶制剂和重组微生物将不同的起始组合物转化为目标甜菊糖苷。高度纯化的瑞鲍迪苷用作可食用和可咀嚼组合物例如任意饮料,糖食,焙烤食品,饼干和口香糖中的无热量甜味剂,风味增强剂,甜味增强剂和泡沫抑制剂。
Description
技术领域
本发明涉及用于制备包含甜菊糖苷的组合物(包括高度纯化的甜菊糖苷组合物)的方法。
发明背景
高强度甜味剂具有大于蔗糖甜味水平许多倍的甜味水平。它们主要为无热量的,并且常用于膳食和低热量产品,包括食品和饮料。高强度甜味剂不会引起升胰岛素响应,使得它们适用于目标在于糖尿病的产品和其他有益于控制其糖类摄入的产品。
甜菊糖苷为南美某些地区土生土长的菊科(Asteraceae)(菊科(Compositae))的多年生灌木甜叶菊(Stevia rebaudiana Bertoni)叶中发现的一类化合物。它们的结构特征在于单碱基甜菊醇,其区别在于在C13和C19位置处存在糖类残基。它们蓄积在甜菊属(Stevia)叶中,占总干重的大约10%-20%。基于干重,在甜菊属叶中发现的4种主要糖苷典型地包括甜菊苷(9.1%),瑞鲍迪苷A(3.8%),瑞鲍迪苷C(0.6-1.0%)和杜克苷A(0.3%)。其他已知的甜菊糖苷包括瑞鲍迪苷B,C,D,E,F和M,甜菊双糖苷和甜茶苷。
尽管已知由甜叶菊制备甜菊糖苷的方法,但是这些方法中的许多在商业上不适用。
因此,仍然需要简单,有效和具有经济性的用于制备包含甜菊糖苷的组合物(包括高度纯化的甜菊糖苷组合物)的方法。
发明概述
本发明提供了用于制备包含目标甜菊糖苷的组合物的方法,所述方法通过使包含有机底物的起始组合物与微生物细胞和/或酶制剂接触来进行,由此产生包含目标甜菊糖苷的组合物。
起始组合物可以为包含至少一个碳原子的任意有机化合物。在一个实施方案中,起始组合物选自甜菊糖苷,多元醇或糖醇,各种糖类。
目标甜菊糖苷可以为任意甜菊糖苷。在一个实施方案中,目标甜菊糖苷为甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3,瑞鲍迪苷AM或合成甜菊糖苷。
在一个实施方案中,目标甜菊糖苷为瑞鲍迪苷AM。
在一些优选的实施方案中,使用包含一种或多种酶的酶制剂或包含一种或多种酶的微生物细胞,其能够将起始组合物转化为目标甜菊糖苷。所述酶可以位于细胞表面上和/或其内部。所述酶制剂可以以完整细胞混悬液,粗的裂解物或作为纯化的酶提供。该酶制剂可以为游离形式或固定在由无机物或有机物制成的固体支持物上。
在一些实施方案中,微生物细胞包含将起始组合物转化为目标甜菊糖苷的必不可少的酶和编码它们的基因。因此,本发明还提供了用于制备包含目标甜菊糖苷的组合物的方法,所述方法通过使包含有机底物的起始组合物包含至少一种酶的微生物细胞接触来进行,所述至少一种酶能够将起始组合物转化为目标甜菊糖苷,由此产生包含至少一种目标甜菊糖苷的介质。
将起始组合物转化为目标甜菊糖苷必不可少的酶包括甜菊醇生物合成酶,UDP-葡糖基转移酶(UGT)和/或UDP-再循环酶。
在一个实施方案中,甜菊醇生物合成酶包括甲羟戊酸(MVA)途径酶。
在另一个实施方案中,甜菊醇生物合成酶包括非甲羟戊酸2-C-甲基-D-赤藓糖醇-4-磷酸途径(MEP/DOXP)酶。
在一个实施方案中,甜菊醇生物合成酶选自:香叶基香叶基二磷酸合酶,柯巴基二磷酸合酶(copalyl diphosphate synthase),贝壳杉烯合酶,贝壳杉烯氧化酶,贝壳杉烯酸13-羟化酶(KAH),甜菊醇合成酶,脱氧木酮糖5-磷酸合酶(DXS),D-1-脱氧木酮糖5-磷酸还原异构酶(DXR),4-二磷酸胞嘧啶基(diphosphocytidyl)-2-C-甲基-D-赤藓糖醇合酶(CMS),4-二磷酸胞嘧啶基-2-C-甲基-D-赤藓糖醇激酶(CMK),4-二磷酸胞嘧啶基-2-C-甲基-D-赤藓糖醇2,4-环二磷酸合酶(MCS),l-羟基-2-甲基-2(E)-丁烯基4-二磷酸合酶(HDS),l-羟基-2-甲基-2(E)-丁烯基4-二磷酸还原酶(HDR),乙酰乙酰基-CoA硫解酶,截短型HMG-CoA还原酶,甲羟戊酸激酶,磷酸甲羟戊酸激酶,甲羟戊酸焦磷酸脱羧酶,细胞色素P450还原酶等。
UDP-葡糖基转移酶可以为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇和/或甜菊糖苷底物上,以提供目标甜菊糖苷。
如下文所用,除非另有指定,否则术语“SuSy_AT”是指具有如实施例1中所述的氨基酸序列“SEQ ID 1”的蔗糖合酶。
如下文所用,除非另有指定,否则术语“UGTSl2”是指具有如实施例1中所述的氨基酸序列“SEQ ID 2”的UDP-葡糖基转移酶。
如下文所用,术语“UGT76G1”除非另有指定,否则是指具有如实施例1中所述的氨基酸序列“SEQ ID 3”的UDP-葡糖基转移酶。
在一个实施方案中,甜菊醇生物合成酶和UDP-葡糖基转移酶在微生物细胞中产生。微生物细胞可以为,例如大肠杆菌(E.coli),酵母属(Saccharomyces sp.),曲霉属(Aspergillus sp.),毕赤酵母属(Pichia sp.),芽孢杆菌属(Bacillus sp.),耶罗威亚酵母属(Yarrowia sp.)等。在另一个实施方案中,合成了UDP-葡糖基转移酶。
在一个实施方案中,UDP-葡糖基转移酶选自:UGT74G1,UGT85C2,UGT76G1,UGT91D2,UGTSl2,EUGT11和UGT,其具有与这些多肽具有显著(>85%,>86%,>87%,>88%,>89%,>90%,>91%,>92%,>93%,>94%,>95%,>96%,>97%,>98%,>99%)氨基酸序列同一性;以及编码这些UGT的分离的核酸分子。
在一个实施方案中,甜菊醇生物合成酶,UGT和UDP-葡萄糖再循环系统存在于一种微生物(微生物细胞)中。微生物可以为,例如大肠杆菌,酵母属,曲霉属,毕赤酵母属,芽孢杆菌属,耶罗威亚酵母属。
在一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇上或在C13处具有-OH官能团的任意起始甜菊糖苷上,得到在C13处具有-O-葡萄糖β吡喃葡萄糖苷的糖苷键的目标甜菊糖苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇上或在C19处具有-COOH官能团的任意起始甜菊糖苷上,得到在C19处具有-COO-葡萄糖β-吡喃葡萄糖苷的糖苷键的目标甜菊糖苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT74G1或与UGT74G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到任意起始甜菊糖苷的C19处的现有葡萄糖上,得到具有至少一个另外的葡萄糖的目标甜菊糖苷,该葡萄糖在新形成的配糖键处具有至少一个β1→2吡喃葡萄糖苷的糖苷键。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到任意起始甜菊糖苷的C19处的现有葡萄糖上,得到具有至少一个另外的葡萄糖的目标甜菊糖苷,该葡萄糖在新形成的键配糖键上具有至少一个β1→3吡喃葡萄糖苷的糖苷键。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到任意起始甜菊糖苷的C13处的现有葡萄糖上,得到具有至少一个另外的葡萄糖的目标甜菊糖苷,该葡萄糖在新形成的配糖键处具有至少一个β1→2吡喃葡萄糖苷的糖苷键。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇上以形成甜菊单糖苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇上以形成甜菊单糖苷A。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT74G1或与UGT74G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷A上以形成甜菊双糖苷B。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷A上以形成甜菊双糖苷A。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷A上以形成甜茶苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷上以形成甜茶苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT74G1或与UGT74G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷上以形成甜菊双糖苷。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷B上以形成甜菊苷B。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷B上以形成甜菊苷C。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷A上以形成甜菊苷A。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷A上以形成甜菊苷C。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜茶苷上以形成甜菊苷B。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜茶苷上以形成甜菊苷A(瑞鲍迪苷KA)。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜茶苷上以形成甜菊苷。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷上以形成甜菊苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT74G1或与UGT74G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷B上以形成瑞鲍迪苷E3。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷B上以形成瑞鲍迪苷E2。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷A(瑞鲍迪苷KA)上以形成瑞鲍迪苷E3。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷A(瑞鲍迪苷KA)上以形成瑞鲍迪苷E。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷C上以形成瑞鲍迪苷E3。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷上以形成瑞鲍迪苷E2。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷上以形成瑞鲍迪苷E。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到瑞鲍迪苷E3上以形成瑞鲍迪苷AM。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到瑞鲍迪苷E2上以形成瑞鲍迪苷AM。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到瑞鲍迪苷E上以形成瑞鲍迪苷AM。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
任选地,本发明的方法还包括在起始组合物上使用多于一种的UGT,以得到具有比起始组合物多于一个葡萄糖单元的目标甜菊糖苷。在一个具体的实施方案中,UDP-葡糖基转移酶是UGT74G1,UGT85C2,UGT76G1,UGTSl2,EUGT11和/或UGT91D2或任何与UGT74G1,UGT85C2,UGT76G1,UGTSl2,EUGT11和/或UGT91D2具有>85%的氨基酸序列同一性的UGT或其任意组合,其能够将多于一个的葡萄糖单元添加到起始组合物上以得到具有比起始组合物多于一个葡萄糖单元的甜菊糖苷。
在一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将全部两个葡萄糖单元添加到甜菊苷上以形成瑞鲍迪苷AM。在一个具体的实施方案中,UDP-葡糖基转移酶选自UGTSl2,EUGT11,UGT91D2,UGT76G1或任何与UGTSl2,EUGT11,UGT91D2,UGT76G1具有>85%的氨基酸序列同一性的UGT或其任意组合。在另一个具体的实施方案中,UDP-葡糖基转移酶是UGTSl2和UGT76G1。
任选地,本发明的方法还包括使UDP再循环,得到UDP-葡萄糖。在一个实施方案中,该方法包括通过提供再循环催化剂和使底物再循环使UDP再循环,以便使用催化量的UDP-葡糖基转移酶和UDP-葡萄糖将甜菊醇和/或甜菊糖苷底物转化为目标甜菊糖苷。
在一个实施方案中,再循环催化剂为蔗糖合酶SuSy_At或与SuSy_At具有>85%氨基酸序列同一性的蔗糖合酶。
在一个实施方案中,再循环底物为蔗糖。
任选地,本发明的方法还包括应用转糖苷酶,其将寡糖或多糖用作糖供体,以修饰受体目标甜菊糖苷分子。非限制性实例包括环糊精葡糖基转移酶(CGTase),呋喃果糖苷酶,淀粉酶,蔗糖酶,glucosucrase,β-h-果糖苷酶,β-果糖苷酶,蔗糖酶,果糖基转化酶(fructosylinvertase),碱性转化酶,酸性转化酶,呋喃果糖苷酶。在一些实施方案中,葡萄糖和非葡萄糖的糖包括、但不限于果糖,木糖,鼠李糖,阿拉伯糖,脱氧葡萄糖,半乳糖转化为受体目标甜菊糖苷。在一个实施方案中,受体甜菊糖苷为瑞鲍迪苷AM。
任选地,本发明的方法还包括从介质中分离目标甜菊糖苷,得到高度纯化的目标甜菊糖苷组合物。可以通过至少一种适合的方法分离目标甜菊糖苷,例如结晶,通过膜分离分离,离心,提取,色谱分离或这类方法的组合。
在一个实施方案中,目标甜菊糖苷可以在微生物中产生。在另一个实施方案中,目标甜菊糖苷可以在介质中分泌。在另一个实施方案中,可以连续地从介质中取出释放的甜菊糖苷。在另一个实施方案中,在转化反应完成后,分离目标甜菊糖苷。
在一个实施方案中,分离产生组合物,其包含在无水的基础上大于约80%重量的目标甜菊糖苷,即高度纯化的甜菊糖苷组合物。在另一个实施方案中,分离产生组合物,其包含大于约90%重量的目标甜菊糖苷。在具体的实施方案中,组合物包含大于约95%重量的目标甜菊糖苷。在另外的实施方案中,组合物包含大于约99%重量的目标甜菊糖苷。
目标甜菊糖苷可以为任意多晶型或无定形形式,包括水合物,溶剂合物,无水物或其组合。
纯化的目标甜菊糖苷可以作为甜味剂,香味改良剂,具有改良特性的香料和/或发泡抑制剂用于消费产品中。适合的消费产品包括、但不限于食品,饮料,药物组合物,烟草产品,营养保健品组合物,口腔卫生组合物和化妆品组合物。
附图简述
图1显示瑞鲍迪苷AM的化学结构。
图2显示了从甜菊醇生产瑞鲍迪苷AM和各种甜菊糖苷的途径。
图3显示了使用酶UGTSl2和UGT76G1由甜菊糖苷生物催化生产瑞鲍迪苷AM,并伴随着通过蔗糖合酶SuSy_At将UDP再循环为UDP-葡萄糖。
图4显示了使用酶UGT76G1由瑞鲍迪苷E生物催化生产瑞鲍迪苷AM,并伴随着通过蔗糖合酶SuSy_At将UDP再循环为UDP-葡萄糖。
图5显示了甜菊苷的HPLC色谱图。保留时间为25.992分钟的峰对应于甜菊苷。
图6显示了由甜菊苷生物催化生产瑞鲍迪苷AM的产物的HPLC色谱图。保留时间为10.636分钟的峰对应于瑞鲍迪苷AM。
图7显示了瑞鲍迪苷E的HPLC色谱图。保留时间为10.835分钟的峰对应于瑞鲍迪苷E。
图8显示了由瑞鲍迪苷E的生物催化生产瑞鲍迪苷AM的产物的HPLC色谱图。保留时间为10.936分钟和11.442分钟的峰分别对应于瑞鲍迪苷E和瑞鲍迪苷AM。
图9显示了通过甲醇结晶纯化后的瑞鲍迪苷AM的HPLC色谱图。保留时间为10.336分钟的峰对应于瑞鲍迪苷AM。
图10显示瑞鲍迪苷AM的1H NMR光谱(500MHz,吡啶-d5)。
图11显示瑞鲍迪苷AM的HSQC光谱(500MHz,吡啶-d5)。
图12显示瑞鲍迪苷AM的H,H COSY光谱(500MHz,吡啶-d5)。
图13显示瑞鲍迪苷AM的HMBC光谱(500MHz,吡啶-d5)。
图14显示瑞鲍迪苷AM的HSQC-TOCSY光谱(500MHz,吡啶-d5)。
图15a和图15b分别显示瑞鲍迪苷AM的LC色谱图和瑞鲍迪苷AM的质谱。
详细描述
本发明提供了用于制备包含目标甜菊糖苷的组合物的方法,所述方法通过使包含有机底物的起始组合物与微生物细胞和/或酶制剂接触来进行,由此产生包含目标甜菊糖苷的组合物。
本发明的一个目的在于通过由不同起始组合物制备目标甜菊糖苷的生物催化方法,所述目标甜菊糖苷特别地为甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3,瑞鲍迪苷AM或合成甜菊糖苷。
如本文所用,缩写的术语“reb”是指“瑞鲍迪苷”。两个术语具有相同的含义并且可以互换使用。
如本文所用,“生物催化”或“生物催化的”是指天然或遗传改造的生物催化剂的应用,例如酶或包含一种或多种酶的细胞(包括微生物),它们能够对有机化合物进行单一或多个步骤的化学转化。生物催化方法包括发酵,生物合成,生物转化和生物转化方法。分离的酶和全细胞生物催化为本领域公知的。生物催化剂蛋白酶可以为天然存在的或重组的蛋白质。
如本文所用,术语“甜菊糖苷”是指甜菊醇的糖苷,包括、但不限于:天然存在的甜菊糖苷,例如甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3,瑞鲍迪苷AM,合成甜菊糖苷,例如酶促糖基化的甜菊糖苷及其组合。
起始组合物
如本文所用,“起始组合物”是指包含一种或多种含有至少一个碳原子的有机化合物的任意组合物(通常为水溶液)。
在一个实施方案中,起始组合物选自甜菊醇,甜菊糖苷,多元醇和各种糖类。
起始组合物甜菊糖苷选自甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3或甜叶菊植物中存在的甜菊醇的其他糖苷,合成甜菊糖苷例如酶促糖基化的甜菊糖苷及其组合。
在一个实施方案中,起始组合物为甜菊醇。
在另一个实施方案中,起始组合物甜菊糖苷为甜菊单糖苷。
在另一个实施方案中,起始组合物甜菊糖苷为甜菊单糖苷A。
在仍然另一个实施方案中,起始组合物甜菊糖苷为甜茶苷。
在仍然另一个实施方案中,起始组合物甜菊糖苷为甜菊双糖苷。
在仍然另一个实施方案中,起始组合物甜菊糖苷为甜菊双糖苷A。
在仍然另一个实施方案中,起始组合物甜菊糖苷为甜菊双糖苷B。
在另一个实施方案中,起始组合物甜菊糖苷为甜菊苷。
在另一个实施方案中,起始组合物甜菊糖苷为甜菊苷A,也称为瑞鲍迪苷KA。
在仍然另一个实施方案中,起始组合物甜菊糖苷为甜菊苷B。
在仍然另一个实施方案中,起始组合物甜菊糖苷为甜菊苷C。
在另一个实施方案中,起始组合物甜菊糖苷为瑞鲍迪苷E。
在另一个实施方案中,起始组合物甜菊糖苷为瑞鲍迪苷E2。
在另一个实施方案中,起始组合物甜菊糖苷为瑞鲍迪苷E3。
术语“多元醇”是指包含一个以上羟基的分子。多元醇可以是分别包含2,3和4个羟基的二醇,三醇或四醇。多元醇还可以包含多于4个的羟基,例如五元醇,六元醇,七元醇等,其分别包含5个,6个或7个羟基。另外,多元醇也可以是糖醇,多元醇或作为糖类的还原形式的多元醇,其中羰基(醛或酮,还原糖)已被还原为伯或仲羟基。多元醇的实例包括、但不限于赤藓糖醇,麦芽糖醇,甘露糖醇,山梨糖醇,乳糖醇,木糖醇,肌醇,异麦芽酮糖醇,丙二醇,甘油,苏糖醇,半乳糖醇,氢化异麦芽酮糖,还原异麦芽寡糖,还原木寡糖,还原龙胆寡糖,还原麦芽糖浆,还原葡萄糖浆,氢化淀粉水解产物,聚糖醇(polyglycitol)和糖醇或其他任何能够被还原的糖类。
术语“糖类”是指被式(CH2O)n(其中n为3-30)的多个羟基基团取代的醛或酮化合物,以及它们的低聚物和聚合物。此外,本发明的糖类在一个或多个位置上被取代或被脱氧。如本文所用,糖类包括未改性的糖类,糖类衍生物,取代的糖类和改性的糖类。如本文所用,短语“糖类衍生物”,“取代的糖类”和“改性的糖类”是同义词。改性的糖类是指任意糖类,其中至少一个原子被添加,去除或取代的任何糖类或其组合。因此,糖类的衍生物或取代的糖类包括取代和未取代的单糖,二糖,寡糖和多糖。所述糖类衍生物或取代的糖类任选地在任何相应的C-位置脱氧和/或被一个或多个部分取代,所述部分例如氢,卤素,卤代烷基,羧基,酰基,酰氧基,氨基,酰胺基,羧基衍生物,烷基氨基,二烷基氨基,芳基氨基,烷氧基,芳氧基,硝基,氰基,磺基,巯基,亚氨基,磺酰基,亚磺酰基,亚氧硫基,亚磺酰基,氨磺酰基,碳烷氧基,羧酰胺基,膦酰基,次膦酰基,磷酰基,膦基,硫酯,硫醚,肟基,肼基,氨基甲酸酯基,二氧磷基,膦酸酯基或任何其他可行的官能团,它们可提供糖类衍生物或取代的糖类功能,以改善甜味剂组合物的甜味。
可根据本发明使用的糖类的实例包括但不限于塔格糖,海藻糖,半乳糖,鼠李糖,各种环糊精,环状寡糖,各种类型的麦芽糊精,葡聚糖,蔗糖,葡萄糖,核酮糖,果糖,苏糖,阿拉伯糖,木糖,来苏糖,阿洛糖,阿卓糖,甘露糖,艾杜糖,乳糖,麦芽糖,转化糖,异海藻糖,新海藻糖,异麦芽酮糖,赤藓糖,脱氧核糖,古洛糖,艾杜糖,塔洛糖,赤藓酮糖,木酮糖,阿洛酮糖,松二糖,纤维二糖,支链淀粉,葡糖胺,甘露糖胺,岩藻糖,葡糖醛酸,葡糖酸,葡糖酸内酯,阿比可糖,半乳糖胺,甜菜寡糖,异麦芽寡糖(异麦芽糖,异麦芽三糖,潘糖等),木寡糖(木三糖,木二糖等),木糖终止的寡糖,龙胆寡糖(龙胆二糖,龙胆三糖,龙胆四糖等),山梨糖,黑曲霉寡糖,帕拉金糖寡糖,果寡糖(蔗果三糖,蔗果四糖等),麦芽四醇,麦芽三醇,麦芽寡糖(麦芽三糖,麦芽四糖,麦芽五糖,麦芽六糖,麦芽七糖等),淀粉,菊粉,菊寡糖,乳果糖,蜜二糖,棉子糖,核糖,异构化的液体糖例如高果糖玉米糖浆,偶联糖和大豆寡糖。另外,本文所用的糖类可以呈D-构型或L-构型。
起始组合物可以为合成或纯化的(部分或完全),商购的或制备的。
在一个实施方案中,起始组合物为甘油。
在另一个实施方案中,起始组合物为葡萄糖。
在另一个实施方案中,起始组合物为蔗糖。
在另一个实施方案中,起始组合物为淀粉。
在另一个实施方案中,起始组合物为麦芽糖糊精。
在另一个实施方案中,起始组合物为纤维素。
在另一个实施方案中,起始组合物为直链淀粉。
起始组合物的有机化合物用作生产如本文所述的目标甜菊糖苷的底物。
目标甜菊糖苷
本发明的目标甜菊糖苷可以为可以通过本文公开的方法制备的任意甜菊糖苷。在一个实施方案中,目标甜菊糖苷选自甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3,瑞鲍迪苷AM,或在甜叶菊植物中存在的甜菊醇的其他糖苷,合成甜菊糖苷例如酶促糖基化的甜菊糖苷及其组合。
在一个实施方案中,目标甜菊糖苷为甜菊单糖苷。
在另一个实施方案中,目标甜菊糖苷为甜菊单糖苷A。
在另一个实施方案中,目标甜菊糖苷为甜菊双糖苷。
在另一个实施方案中,目标甜菊糖苷为甜菊双糖A。
在另一个实施方案中,目标甜菊糖苷为甜菊双糖苷B。
在另一个实施方案中,目标甜菊糖苷为甜茶苷。
在另一个实施方案中,目标甜菊糖苷为甜菊苷。
在另一个实施方案中,目标甜菊糖苷为甜菊苷A(瑞鲍迪苷KA)。
在另一个实施方案中,目标甜菊糖苷为甜菊苷B。
在另一个实施方案中,目标甜菊糖苷为甜菊苷C。
在另一个实施方案中,目标甜菊糖苷为瑞鲍迪苷E。
在另一个实施方案中,目标甜菊糖苷为瑞鲍迪苷E2。
在另一个实施方案中,目标甜菊糖苷为瑞鲍迪苷E3。
在另一个实施方案中,目标甜菊糖苷为瑞鲍迪苷AM。
目标甜菊糖苷可以为任意多晶型或无定形形式,包括水合物,溶剂合物,无水物或其组合。
在一个实施方案中,本发明为用于生产甜菊单糖苷的生物催化方法。
在一个实施方案中,本发明为用于生产甜菊单糖苷A的生物催化方法。
在一个实施方案中,本发明为用于生产甜菊双糖苷的生物催化方法。
在一个实施方案中,本发明为用于生产甜菊双糖苷A的生物催化方法。
在一个实施方案中,本发明为用于生产的生物催化方法甜菊双糖苷B。
在一个实施方案中,本发明为用于生产甜茶苷的生物催化方法。
在一个实施方案中,本发明为用于生产甜菊苷的生物催化方法。
在一个实施方案中,本发明为用于生产甜菊苷A(瑞鲍迪苷KA)的生物催化方法。
在一个实施方案中,本发明为用于生产甜菊苷B的生物催化方法。
在一个实施方案中,本发明为用于生产甜菊苷C的生物催化方法。
在一个实施方案中,本发明为用于生产瑞鲍迪苷E的生物催化方法。
在一个实施方案中,本发明为用于生产瑞鲍迪苷E2的生物催化方法。
在一个实施方案中,本发明为用于生产瑞鲍迪苷E3的生物催化方法。
在一个实施方案中,本发明为用于生产瑞鲍迪苷AM的生物催化方法。
在一个具体的实施方案中,本发明提供由包含甜菊苷和UDP-葡萄糖的起始组合物生产瑞鲍迪苷AM的生物催化方法。
在另一个具体的实施方案中,本发明提供由包含瑞鲍迪苷E和UDP-葡萄糖的起始组合物生产瑞鲍迪苷AM的生物催化方法。
任选地,本发明的方法还包括从介质中分离目标甜菊糖苷,得到高度纯化的目标甜菊糖苷组合物。目标甜菊糖苷可以通过任意适合的方法分离,例如结晶,通过膜分离,离心,提取,色谱分离或这类方法的组合。
在具体的实施方案中,本文所述方法产生高度纯化的目标甜菊糖苷组合物。如本文所用,术语“高度纯化的”是指在无水(干燥)的基础上的具有大于约80%重量的目标甜菊糖苷的组合物。在一个实施方案中,高度纯化的目标甜菊糖苷组合物包含在无水(干燥)的基础上的大于约90%重量的目标甜菊糖苷,例如基于干重大于约91%,大于约92%,大于约93%,大于约94%,大于约95%,大于约96%,大于约97%,大于约98%或大于约99%的目标甜菊糖苷含量。
在一个实施方案中,当目标甜菊糖苷为reb AM时,本文所述的方法提供具有基于干重大于约90%reb AM含量的组合物。在另一个具体的实施方案中,当目标甜菊糖苷为rebAM时,本文所述的方法提供包含基于干重大于约95%reb AM含量的组合物。
微生物和酶制剂
在本发明的一个实施方案中,使微生物(微生物细胞)和/或酶制剂与包含起始组合物的介质接触,产生目标甜菊糖苷。
所述酶以完整细胞混悬液,粗裂解物,纯化的酶或其组合的形式提供。在一个实施方案中,所述生物催化剂为纯化的酶,其能够将起始组合物转化为目标甜菊糖苷。在另一个实施方案中,所述生物催化剂为粗裂解物,其包含至少一种能够将起始组合物转化为目标甜菊糖苷的酶。在另一个实施方案中,所述生物催化剂为完整细胞混悬液,其包含能够将起始组合物转化为目标甜菊糖苷的至少一种酶。
在另一个实施方案中,所述生物催化剂为一种或多种微生物细胞,其包含能够将起始组合物转化为目标甜菊糖苷的酶。所述酶位于细胞表面上,细胞内部或位于细胞表面上和细胞内部。
用于将起始组合物转化为目标甜菊糖苷的适合的酶包括、但不限于甜菊醇生物合成酶和UDP-葡糖基转移酶(UGT)。任选地,其可以包括UDP-再循环酶。
在一个实施方案中,甜菊醇生物合成酶包括甲羟戊酸(MVA)途径酶。
在另一个实施方案中,甜菊醇生物合成酶包括非甲羟戊酸2-C-甲基-D-赤藓糖醇-4-磷酸途径(MEP/DOXP)酶。
在一个实施方案中,甜菊醇生物合成酶选自:香叶基香叶基二磷酸合酶,柯巴基二磷酸合酶,贝壳杉烯合酶,贝壳杉烯氧化酶,贝壳杉烯酸13-羟化酶(KAH),甜菊醇合成酶,脱氧木酮糖5-磷酸合酶(DXS),D-1-脱氧木酮糖5-磷酸还原异构酶(DXR),4-二磷酸胞嘧啶基-2-C-甲基-D-赤藓糖醇合酶(CMS),4-二磷酸胞嘧啶基-2-C-甲基-D-赤藓糖醇激酶(CMK),4-二磷酸胞嘧啶基-2-C-甲基-D-赤藓糖醇2,4-环二磷酸合酶(MCS),l-羟基-2-甲基-2(E)-丁烯基4-二磷酸合酶(HDS),l-羟基-2-甲基-2(E)-丁烯基4-二磷酸还原酶(HDR),乙酰乙酰基-CoA硫解酶,截短型HMG-CoA还原酶,甲羟戊酸激酶,磷酸甲羟戊酸激酶,甲羟戊酸焦磷酸脱羧酶,细胞色素P450还原酶等。
UDP-葡糖基转移酶可以为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇和/或甜菊糖苷底物上,以提供目标甜菊糖苷。
在一个实施方案中,甜菊醇生物合成酶和UDP-葡糖基转移酶在微生物细胞中产生。所述微生物细胞可以为,例如大肠杆菌,酵母属,曲霉属,毕赤酵母属,芽孢杆菌属和耶罗威亚酵母属等。在另一个实施方案中,UDP-葡糖基转移酶为合成的。
在一个实施方案中,UDP-葡糖基转移酶选自:UGT74G1,UGT85C2,UGT76G1,UGT91D2,UGTSl2,EUGT11和与这些些多肽具有显著(>85%,>86%,>87%,>88%,>89%,>90%,>91%,>92%,>93%,>94%,>95%,>96%,>97%,>98%,>99%)氨基酸序列同一性的UGT以及编码这些UGT的分离的核酸分子。
在一个实施方案中,甜菊醇生物合成酶,UGT和UDP-葡萄糖再循环系统存在于一种微生物(微生物细胞)中。所述微生物可以为,例如大肠杆菌,酵母属,曲霉属,毕赤酵母属,芽孢杆菌属和耶罗威亚酵母属。
在一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇或在C13处带有-OH官能团的任意起始甜菊糖苷上,得到在C13处具有-O-葡萄糖β吡喃葡萄糖苷的糖苷键的目标甜菊糖苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇或在C19处带有-COOH官能团的任意起始甜菊糖苷上,得到在C19处具有-COO-葡萄糖β-吡喃葡萄糖苷的糖苷键的目标甜菊糖苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT74G1或与UGT74G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到任意起始甜菊糖苷的C19处的现有葡萄糖上,得到具有至少一个另外的葡萄糖的目标甜菊糖苷,该葡萄糖在新形成的糖苷键处具有至少一个β1→2吡喃葡萄糖苷的糖苷键。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到任意起始甜菊糖苷的C19处的现有葡萄糖上,得到具有至少一个另外的葡萄糖的目标甜菊糖苷,该葡萄糖在新形成的糖苷键处具有至少一个β1→3吡喃葡萄糖苷的糖苷键。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到任意起始甜菊糖苷的C13处的现有葡萄糖上,得到具有至少一个另外的葡萄糖的目标甜菊糖苷,该葡萄糖在新形成的糖苷键处具有至少一个β1→2吡喃葡萄糖苷的糖苷键。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇上以形成甜菊单糖苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊醇上以形成甜菊单糖苷A。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT74G1或与UGT74G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷A上以形成甜菊双糖苷B。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷A上以形成甜菊双糖苷A。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷A上以形成甜茶苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷上以形成甜茶苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT74G1或与UGT74G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊单糖苷上以形成甜菊双糖苷。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷B上以形成甜菊苷B。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷B上以形成甜菊苷C。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷A上以形成甜菊苷A。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷A上以形成甜菊苷C。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜茶苷上以形成甜菊苷B。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜茶苷上以形成甜菊苷A(瑞鲍迪苷KA)。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜茶苷上以形成甜菊苷。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊双糖苷上以形成甜菊苷。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT74G1或与UGT74G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷B上以形成瑞鲍迪苷E3。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷B上以形成瑞鲍迪苷E2。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷A(瑞鲍迪苷KA)上以形成瑞鲍迪苷E3。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷A(瑞鲍迪苷KA)上以形成瑞鲍迪苷E。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷C上以形成瑞鲍迪苷E3。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT85C2或与UGT85C2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷上以形成瑞鲍迪苷E2。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到甜菊苷上以形成瑞鲍迪苷E。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到瑞鲍迪苷E3上以形成瑞鲍迪苷AM。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到瑞鲍迪苷E2上以形成瑞鲍迪苷AM。在一个具体的实施方案中,UDP-葡糖基转移酶为UGTSl2或与UGTSl2具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为EUGT11或与EUGT11具有>85%的氨基酸序列同一性的UGT。在另一个具体的实施方案中,UDP-葡糖基转移酶为UGT91D2或与UGT91D2具有>85%的氨基酸序列同一性的UGT。
在另一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将至少一个葡萄糖单元添加到瑞鲍迪苷E上以形成瑞鲍迪苷AM。在一个具体的实施方案中,UDP-葡糖基转移酶为UGT76G1或与UGT76G1具有>85%的氨基酸序列同一性的UGT。
任选地,本发明的方法还包括在起始组合物上使用多于一种的UGT,以得到具有比起始组合物多于一个葡萄糖单元的目标甜菊糖苷。在一个具体的实施方案中,UDP-葡糖基转移酶是UGT74G1,UGT85C2,UGT76G1,UGTSl2,EUGT11和/或UGT91D2或任何与UGT74G1,UGT85C2,UGT76G1,UGTSl2,EUGT11和/或UGT91D2具有>85%的氨基酸序列同一性的UGT或其任意组合,其能够将多于一个的葡萄糖单元添加到起始组合物上以得到具有比起始组合物多于一个葡萄糖单元的甜菊糖苷。
在一个实施方案中,UDP-葡糖基转移酶为任意UDP-葡糖基转移酶,其能够将全部两个葡萄糖单元添加到甜菊苷上以形成瑞鲍迪苷AM。在一个具体的实施方案中,UDP-葡糖基转移酶选自UGTSl2,EUGT11,UGT91D2,UGT76G1或任何与UGTSl2,EUGT11,UGT91D2,UGT76G1具有>85%的氨基酸序列同一性的UGT或其任意组合。在另一个具体的实施方案中,UDP-葡糖基转移酶是UGTSl2和UGT76G1。
任选地,本发明的方法还包括再循环UDP,得到UDP-葡萄糖。在一个实施方案中,该方法包括通过提供再循环催化剂和再循环底物再循环UDP,以便使用催化量的UDP-葡糖基转移酶和UDP-葡萄糖将甜菊醇和/或甜菊糖苷底物生物转化为目标甜菊糖苷。UDP再循环酶可以是蔗糖合酶SuSy_At或与SuSy_At具有>85%的氨基酸序列同一性的蔗糖合酶,并且在循环底物可以是蔗糖。
任选地,本发明的方法还包括应用转糖苷酶,其使用寡糖或多糖作为糖供体,以便修饰受体目标甜菊糖苷分子。非限制性实例包括环糊精糖基转移酶(CGTase),呋喃果糖苷酶,淀粉酶,蔗糖酶,glucosucrase,β-h-果糖苷酶,β-果糖苷酶,蔗糖酶,果糖基转化酶,碱性转化酶,酸性转化酶,呋喃果糖苷酶。在一些实施方案中,葡萄糖和非葡萄糖的糖包括、但不限于果糖,木糖,鼠李糖,阿拉伯糖,脱氧葡萄糖,半乳糖转化为受体目标甜菊糖苷。在一个实施方案中,受体甜菊糖苷为瑞鲍迪苷AM。
在另一个实施方案中,能够将至少一个葡萄糖单元添加到起始组合物甜菊糖苷上的UDP-葡糖基转移酶与UGT具有>85%的氨基酸序列同一性,所述UGT选自如下列表GenInfo识别码,优选自表1和
表2。
表1
表2
GI编号 | 保藏号 | 来源 | 内部参比物 |
460409128 | XP.004249992.1 | 番茄 | UGTSl |
460386018 | XP.004238697.1 | 番茄 | - |
460409134 | XP.004249995.1 | 番茄 | - |
460410132 | XP.004250485.1 | 番茄 | UGTSl2 |
460410130 | XP.004250484.1 | 番茄 | - |
460410128 | XP.004250483.1 | 番茄 | - |
460378310 | XP.004234916.1 | 番茄 | - |
209954733 | BAG80557.1 | 枸杞(Lycium barbarum) | UGTLB |
209954725 | BAG80553.1 | 枸杞 | - |
本发明的一个实施方案为包含酶的微生物细胞,即能够将起始组合物转化为目标甜菊糖苷的酶。因此,本方法的一些实施方案包括使微生物与包含起始组合物的介质接触,得到包含至少一种目标甜菊糖苷的介质。
所述微生物可以为任意微生物,其具有将起始组合物转化为目标甜菊糖苷的必不可少的酶。这些酶在微生物基因组内被编码。
适合的微生物包括、但不限于大肠杆菌,酵母属,曲霉属,毕赤酵母属,芽孢杆菌属和耶罗威亚酵母属等。
在一个实施方案中,当与起始组合物接触时,所述微生物为游离的。
在另一个实施方案中,当与起始组合物接触时,所述微生物为固定的。例如,可以将所述微生物固定在由无机物或有机物制成的固体支持物上。固体支持物的非限制性实例包括衍生的纤维素或玻璃,金属氧化物或膜。例如,可以通过共价结合,吸附,交联,俘获或封装将微生物固定在固体支持物上。
在另一个实施方案中,能够将起始组合物转化为目标甜菊糖苷的酶从微生物中分泌出来并且进入反应介质。
任选地纯化目标甜菊糖苷。从反应介质中纯化目标甜菊糖苷可以通过至少一种适合的方法进行,得到高度纯化的目标甜菊糖苷组合物。适合的方法包括结晶,通过膜分离,离心,提取(液相或固相),色谱分离,HPLC(制备型或分析型)或这类方法的组合。
用途
根据本发明得到的高度纯化的目标糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以“照此”使用,或与另外的甜味剂,香料,食品成分及其组合组合使用。
香料的非限制性实例包括、但不限于来檬,柠檬,橙,水果,香蕉,葡萄,梨,菠萝,芒果,浆果,苦杏仁,可乐,肉桂,糖,棉糖,香草及其组合。
另外的食品成分的非限制性实例包括、但不限于酸化剂,有机和氨基酸,着色剂,填充剂,改性淀粉,树胶,组织形成剂,防腐剂,咖啡碱,抗氧化剂,乳化剂,稳定剂,增稠剂,胶凝剂及其组合。
可以将根据本发明得到的高度纯化的目标糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM制备成各种多晶型形式,包括、但不限于水合物,溶剂合物,无水物,无定形形式及其组合。
根据本发明得到的高度纯化的目标糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以作为高强度天然甜味剂掺入食品,饮料,药物组合物,化妆品,口香糖,桌面产品(tabletop product),谷物,乳制品,牙膏和其他口腔组合物等中。
根据本发明得到的高度纯化的目标糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以作为甜味化合物作为唯一的甜味剂使用,或可以与至少一种天然存在的高强度甜味剂联用,例如瑞鲍迪苷A,瑞鲍迪苷A2,瑞鲍迪苷A3,瑞鲍迪苷B,瑞鲍迪苷C,瑞鲍迪苷C2,瑞鲍迪苷D,瑞鲍迪苷D2,瑞鲍迪苷F,瑞鲍迪苷F2,瑞鲍迪苷F3,瑞鲍迪苷G,瑞鲍迪苷H,瑞鲍迪苷I,瑞鲍迪苷I2,瑞鲍迪苷I3,瑞鲍迪苷J,瑞鲍迪苷K,瑞鲍迪苷K2,瑞鲍迪苷L,瑞鲍迪苷M,瑞鲍迪苷M2,瑞鲍迪苷N,瑞鲍迪苷O,瑞鲍迪苷O2,瑞鲍迪苷Q,瑞鲍迪苷Q2,瑞鲍迪苷Q3,瑞鲍迪苷R,瑞鲍迪苷S,瑞鲍迪苷T,瑞鲍迪苷T1,瑞鲍迪苷U,瑞鲍迪苷U2,瑞鲍迪苷V,瑞鲍迪苷W,瑞鲍迪苷W2,瑞鲍迪苷W3,瑞鲍迪苷Y,瑞鲍迪苷Z1,瑞鲍迪苷Z2,杜克苷A,杜克苷C,甜菊苷D,甜菊苷E,甜菊苷E2,甜菊苷F,罗汉果苷,甜味蛋白,新橙皮苷二氢查耳酮,甘草酸及其盐,奇异果甜蛋白,紫苏葶,皮尔南甘素(pernandulcin),无患子倍半萜苷(mukuroziosides),白元参苷,糙苏苷-I,二甲基-六氢芴-二羧酸,相思子三萜苷,巴西甘草甜素,肉质雪胆皂苷(carnosiflosides),青钱柳苷,裂环达玛烷型三萜苷(pterocaryosides),聚波朵苷A,巴西红木素,贺兰甜精(hernandulcin),菲络杜辛(phillodulcin),菝葜苷,根皮苷,三叶苷,二氢黄酮醇,二氢槲皮素-3-乙酸酯,新落新妇苷(neoastilibin),反式-肉桂醛,莫纳甜及其盐,修藤精A(selligueain A),苏木素,莫内甜蛋白,水龙骨甜素,蝶卡苷A(pterocaryoside A),蝶卡苷B,马槟榔甜蛋白,培它丁(pentadin),改味糖蛋白,仙茅甜蛋白,新仙茅甜蛋白(neoculin),绿原酸,西那林,罗汉果甜味剂,罗汉果苷V,赛门苷及其组合。
在一个具体的实施方案中,甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以用于甜味剂组合物中,该组合物包含选自如下的化合物:瑞鲍迪苷A,瑞鲍迪苷A2,瑞鲍迪苷A3,瑞鲍迪苷B,瑞鲍迪苷C,瑞鲍迪苷C2,瑞鲍迪苷D,瑞鲍迪苷D2,瑞鲍迪苷F,瑞鲍迪苷F2,瑞鲍迪苷F3,瑞鲍迪苷G,瑞鲍迪苷H,瑞鲍迪苷I,瑞鲍迪苷I2,瑞鲍迪苷I3,瑞鲍迪苷J,瑞鲍迪苷K,瑞鲍迪苷K2,瑞鲍迪苷L,瑞鲍迪苷M,瑞鲍迪苷M2,瑞鲍迪苷N,瑞鲍迪苷O,瑞鲍迪苷O2,瑞鲍迪苷Q,瑞鲍迪苷Q2,瑞鲍迪苷Q3,瑞鲍迪苷R,瑞鲍迪苷S,瑞鲍迪苷T,瑞鲍迪苷T1,瑞鲍迪苷U,瑞鲍迪苷U2,瑞鲍迪苷V,瑞鲍迪苷W,瑞鲍迪苷W2,瑞鲍迪苷W3,瑞鲍迪苷Y,瑞鲍迪苷Z1,瑞鲍迪苷Z2,杜克苷A,杜克苷C,甜菊苷D,甜菊苷E,甜菊苷E2,甜菊苷F,NSF-02,罗汉果苷V,罗汉果,阿洛酮糖,阿罗糖,D-塔格糖,赤藓糖醇及其组合。
高度纯化的目标糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM还可以与合成高强度甜味剂联用,例如三氯蔗糖,乙酰磺胺酸钾,阿斯巴甜,阿力甜,糖精,新橙皮苷二氢查耳酮,环己氨磺酸盐,纽甜,甘素,suosan advantame及其盐及其组合。
此外,高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以与天然甜味剂抑制剂联用,例如匙羹藤酸,勿甜素,ziziphin,降甜香精(lactisole)等。甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM还可以与各种鲜味增强剂联用。甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以与鲜味和甜味氨基酸混合,例如谷氨酸,天冬氨酸,甘氨酸,丙氨酸,苏氨酸,脯氨酸,丝氨酸,谷氨酸,赖氨酸,色氨酸及其组合。
高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以与一种或多种添加剂联用,所述甜味剂选自糖类,多元醇,氨基酸及其相应的盐,聚氨基酸及其相应的盐,糖酸及其相应的盐,核苷酸,有机酸,无机酸,有机盐,包括有机酸盐和有机碱盐,无机盐,苦味化合物,香料和调味剂成分,收敛化合物,蛋白质或蛋白水解产物,表面活性剂,乳化剂,类黄酮,醇,聚合物及其组合。
高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以与多元醇或糖醇联用。术语“多元醇”是指包含不止一个羟基的分子。多元醇可以是分别含有2,3和4个羟基的二醇,三醇或四醇。多元醇还可含有多于四个羟基,例如五元醇,六元醇,七元醇等,其分别含有5,6或7个羟基。另外,多元醇也可以是糖醇,多元醇或作为糖的还原形式的多元醇,其中羰基(醛或酮,还原糖)已被还原成伯或仲羟基。多元醇的实例包括、但不限于赤藓糖醇,麦芽糖醇,甘露糖醇,山梨糖醇,乳糖醇,木糖醇,肌醇,异麦芽酮糖,丙二醇,甘油,苏糖醇,半乳糖醇,氢化异麦芽酮糖,还原异麦芽寡糖,还原木寡糖,还原龙胆寡糖,还原麦芽糖浆,还原葡萄糖浆,氢化淀粉水解产物,聚糖醇和糖醇或任何其他能够还原的糖类,它们不会对甜味剂组合物的味道产生不利影响。
高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以与低热量甜味剂联用,例如D-塔格糖,L-糖,L-山梨糖,L-阿拉伯糖及其组合。
高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM还可以与各种糖类联用。术语“糖类”通常是指具有式(CH2O)n(其中n为3-30)的被多个羟基取代的醛或酮化合物,以及其寡聚物和聚合物。另外,本发明的糖类可以在一个或多个位置被取代或脱氧。如本文中所用,糖类包括未改性的糖类,糖类衍生物,取代的糖类和改性的糖类。如本文中所用,短语“糖类衍生物”,“取代的糖类”和“改性的糖类”是同义词。改性的糖类意指其中已经添加,去除或取代了至少一个原子或其组合的任何糖类。因此,糖类衍生物或取代的糖类包括取代的和未取代的单糖,二糖,寡糖和多糖。糖类衍生物或取代的糖类可以任选地在任何相应的C-位脱氧,和/或被一个或多个部分(例如氢,卤素,卤代烷基,羧基,酰基,酰氧基,氨基,酰胺基,羧基衍生物,烷基氨基,二烷基氨基,芳基氨基,烷氧基,芳氧基,硝基,氰基,磺基,巯基,亚氨基,磺酰基,亚磺酰基,亚氧硫基,氨磺酰基,烷氧羰基,羧酰胺基,膦酰基,氧膦基,磷酰基,膦基,硫酯,硫醚,肟基,肼基,氨甲酰基,磷,膦酸酯基或任何其他可行的官能团)取代,只要所述糖类衍生物或取代的糖类起着改善甜味剂组合物的甜味即可。
根据本发明使用的糖类的实例包括、但不限于:阿洛酮糖,松二糖,阿洛糖,塔格糖,海藻糖,半乳糖,鼠李糖,各种环糊精,环状寡糖,各种类型的麦芽糊精,葡聚糖,蔗糖,葡萄糖,核酮糖,果糖,苏糖,阿拉伯糖,木糖,来苏糖,阿洛糖,阿卓糖,甘露糖,艾杜糖,乳糖,麦芽糖,转化糖,异海藻糖,新海藻糖,异麦芽酮糖,赤藓糖,脱氧核糖,古洛糖,艾杜糖,塔洛糖,赤藓酮糖,木酮糖,阿洛酮糖,松二糖,纤维二糖,支链淀粉,葡糖胺,甘露糖胺,岩藻糖,葡糖醛酸,葡糖酸,葡糖酸内酯,阿比可糖,半乳糖胺,甜菜寡糖,异麦芽寡糖(异麦芽糖,异麦芽三糖,潘糖等),木寡糖(木三糖,木二糖等),木糖终止的寡糖,龙胆寡糖(龙胆二糖,龙胆三糖,龙胆四糖等),山梨糖,黑曲霉寡糖,帕拉金糖寡糖,果寡糖(蔗果三糖,蔗果四糖等),麦芽四醇,麦芽三醇,麦芽寡糖(麦芽三糖,麦芽四糖,麦芽五糖,麦芽六糖,麦芽七糖等),淀粉,菊粉,菊寡糖,乳果糖,蜜二糖,棉子糖,核糖,异构化的液体糖例如高果糖玉米糖浆,偶联糖和大豆寡糖。另外,本文所用的糖类可以呈D-构型或L-构型。
根据本发明得到的高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以与各种生理学活性物质或功能性成分联用。功能成分通常分为例如以下几类:类胡萝卜素,膳食纤维,脂肪酸,皂苷,抗氧化剂,营养保健品,类黄酮,异硫氰酸盐,酚类,植物固醇和甾烷醇(植物甾醇和植物甾烷醇);多元醇;益生元,益生菌;植物雌激素;大豆蛋白;硫化物/硫醇;氨基酸;蛋白质;维生素和矿物质。功能性成分还可以基于其健康益处(例如心血管,降低胆固醇和消炎)进行分类。在WO2013/096420(其内容由此通过引用并入)中提供了示例性的功能性成分。
根据本发明得到的高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以用作高强度甜味剂,以便产生具有改善的味道特性的零热量,低热量或糖尿病患者用饮料和食品。其还可以用于饮料,食品,药物和其他不能使用糖的产品。此外,高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以作为甜味剂,不仅用于人消费专用的饮料,食品和其他产品,而且用于具有改善特性的动物饲料和草料。
根据本发明得到的高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以用作风味改良剂,以生产具有改良风味的零热量,低热量或糖尿病饮料和食品。当用作风味改良剂或具有改良特性的调味剂(FMP)时,高度纯化的目标甜菊糖苷以低于风味改良剂或FMP的检测水平用于消费产品中。因此,风味改良剂或FMP不会将其自身的可检测到的味道或风味赋予消费产品,而是用来改良消费者对消费产品中其他成分的味道和/或风味的检测。味道和风味改良的一个例子是甜度的增强,其中风味改良剂或FMP本身对消费产品的甜度没有贡献,但可以增强消费者品尝到的甜度的品质。
其中高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以用作风味改良剂或具有改良特性的调味剂的消费产品的实例包括、但不限于酒精饮料,例如伏特加,葡萄酒,啤酒,白酒和清酒等;天然汁;提神饮料;碳酸软饮料;无糖饮料;零热量饮料;热量减少的饮料和食物;酸奶饮料;速溶汁;速溶咖啡;粉状速溶饮料;罐头产品;糖浆;发酵大豆酱;酱油;醋;调味品;蛋黄酱;番茄酱;咖喱;汤;速食肉汤;酱油粉;醋粉;各种类型的饼干;大米饼干;薄脆饼干;面包;巧克力;焦糖;糖果;口香糖;果冻;布丁;果蔬脯;鲜奶油;果酱;柑橘酱;花酱;奶粉;冰淇淋;雪葩;瓶装蔬菜和水果;罐装煮豆;甜汁煮肉和食物;农业蔬菜食品;海味品;火腿;香肠;鱼火腿;鱼香肠;鱼酱;油炸鱼产品;干制海产品;冷冻食品;腌制海藻;腌制肉;烟草;医药产品;以及很多其他食品。原则上其可以有无限的应用。
根据本发明得到的高度纯化的目标甜菊糖苷,特别是甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以用作消泡剂,以生产零热量,低热量或糖尿病的饮料和食品。
其中高度纯化的目标甜菊糖苷,特别是甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以用作甜味化合物的消费产品的实例包括、但不限于:酒精饮料,例如伏特加,葡萄酒,啤酒,白酒和清酒等;天然汁;提神饮料;碳酸软饮料;无糖饮料;零热量饮料;热量减少的饮料和食物;酸奶饮料;速溶汁;速溶咖啡;粉状速溶饮料;罐头产品;糖浆;发酵大豆酱;酱油;醋;调味品;蛋黄酱;番茄酱;咖喱;汤;速食肉汤;酱油粉;醋粉;各种类型的饼干;大米饼干;薄脆饼干;面包;巧克力;焦糖;糖果;口香糖;果冻;布丁;果蔬脯;鲜奶油;果酱;柑橘酱;花酱;奶粉;冰淇淋;雪葩;瓶装蔬菜和水果;罐装煮豆;甜汁煮肉和食物;农业蔬菜食品;海味品;火腿;香肠;鱼火腿;鱼香肠;鱼酱;油炸鱼产品;干制海产品;冷冻食品;腌制海藻;腌制肉;烟草;医药产品;以及很多其他食品。
在例如食品,饮料,药品,化妆品,桌面产品和口香糖等产品的制造过程中,可使用常规方法例如混合,捏合,溶出,酸浸,渗透,渗滤,喷洒,雾化,泡制和其他方法。
此外,根据本发明得到的高度纯化的目标甜菊糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以以干燥或液体形式使用。
可以在食品热处理之前或之后添加高度纯化的目标甜菊糖苷。高度纯化的目标甜菊糖苷,特别是甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM的量取决于用途目的。如上所述,其可以单独或与其他化合物组合使用。
本发明还涉及使用如下化合物作为甜味增强剂的饮料中的甜味增强方法:甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM。因此本发明提供一种饮料,其包含甜味剂和作为甜味增强剂的甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM,其中甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM以在或低于其相应的甜味识别阈值的浓度存在。
如本文中所用,术语“甜味增强剂”是指能够增强或加强组合物例如饮料中的甜味感知的化合物。术语“甜味增强剂(sweetness enhancer)”与术语“甜味增强剂(sweettastepotentiator)”,“甜味增效剂(sweetness potentiator)”,“甜味扩大剂(sweetnessamplifier)”和“甜味强化剂(sweetness intensifier)”同义。
如本文中通常使用的,术语“甜味识别阈值浓度”是可通过人的味觉感知的甜味化合物的最低已知浓度,典型地为约1.0%的蔗糖当量(1.0%的SE)。通常,当以给定甜味增强剂的甜味识别阈值浓度或低于所述浓度存在时,甜味增强剂可增强或加强甜味剂的甜味,而不会自己提供任何明显的甜味;然而,甜味增强剂本身可以在高于其甜味识别阈值浓度的浓度下提供甜味。甜味识别阈值浓度特异于特定的增强剂,并且可根据饮料基质而变化。可通过增加给定增强剂的浓度直至检测到给定饮料基质中的蔗糖当量大于1.0%的味道测试,来容易地确定甜味识别阈值浓度。提供约1.0%蔗糖当量的浓度被认为是甜味识别阈值。
在一些实施方案中,甜味剂以约0.5%至约12%重量的量存在于饮料中,例如约1.0%重量,约1.5%重量,约2.0%重量,约2.5%重量,约3.0%重量,约3.5%重量,约4.0%重量,约4.5%重量,约5.0%重量,约5.5%重量,约6.0%重量,约6.5%重量,约7.0%重量,约7.5%重量,约8.0%重量,约8.5%重量,约9.0%重量,约9.5%重量,约10.0%重量,约10.5%重量,约11.0%重量,约11.5%重量或约12.0%重量。
在一个具体的实施方案中,甜味剂以约0.5%至约10%的量存在于饮料中,例如约2%至约8%重量,约3%至约7%重量,约4%至约6%重量。在一个具体的实施方案中,甜味剂以约0.5%至约8%重量的量存在于饮料中。在另一个具体的实施方案中,甜味剂以约2%至约8%重量的量存在于饮料中。
在一个实施方案中,甜味剂为传统热量的甜味剂。适合的甜味剂包括、但不限于蔗糖,果糖,葡萄糖,高果糖玉米糖浆和高果糖淀粉糖浆。
在另一个实施方案中,甜味剂为赤藓糖醇。
在另一个实施方案中,甜味剂为稀有糖。适合的稀有糖包括、但不限于D-阿洛糖,D-阿洛酮糖,D-核糖,D-塔格糖,L-葡萄糖,L-岩藻糖,L-阿拉伯糖,D-松二糖,D-明串珠菌二糖及其组合。
预期甜味剂可以单独使用,或与其他甜味剂组合使用。
在一个实施方案中,稀有糖是D-阿洛糖。在一个更具体的实施方案中,D-阿洛糖在饮料中的存在量为约0.5%至约10%重量,例如约2%至约8%。
在另一个实施方案中,稀有糖是D-阿洛酮糖。在一个更具体的实施方案中,饮料中的D-阿洛酮糖的存在量为约0.5%至约10%重量,例如约2%至约8%。
在另一个实施方案中,稀有糖是D-核糖。在一个更具体的实施方案中,D-核糖在饮料中的存在量为约0.5%至约10%重量,例如约2%至约8%。
在另一个实施方案中,稀有糖是D-塔格糖。在一个更具体的实施方案中,D-塔格糖在饮料中的存在量为约0.5%至约10%重量,例如约2%至约8%。
在另一个实施方案中,稀有糖是L-葡萄糖。在一个更具体的实施方案中,饮料中的L-葡萄糖的存在量为约0.5%至约10%重量,例如约2%至约8%。
在一个实施方案中,稀有糖是L-岩藻糖。在一个更具体的实施方案中,L-岩藻糖在饮料中的存在量为约0.5%至约10%重量,例如约2%至约8%。
在另一个实施方案中,稀有糖是L-阿拉伯糖。在一个更具体的实施方案中,L-阿拉伯糖在饮料中的存在量为约0.5%至约10%重量,例如约2%至约8%。
在另一个实施方案中,稀有糖是D-松二糖。在一个更具体的实施方案中,D-松二糖在饮料中的存在量为约0.5%至约10%重量,例如约2%至约8%。
在另一个实施方案中,稀有糖是D-明串珠菌二糖。在一个更具体的实施方案中,D-明串珠菌二糖在饮料中的存在量为约0.5%至约10%重量,例如约2%至约8%。
与不存在甜味增强剂的相应饮料相比,以其甜味识别阈值或以下的浓度添加甜味增强剂会增加包含甜味剂和甜味增强剂的饮料的检测到的蔗糖当量。此外,甜味的增加量可以大于包含相同浓度的所述至少一种甜味增强剂而没有任何甜味剂的溶液的可检测甜味。
因此,本发明还提供了用于增强包含甜味剂的饮料的甜味的方法,所述方法包括提供包含甜味剂的饮料,和添加甜味增强剂,其选自甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM或其组合,其中甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM的存在浓度为处于或低于其甜味识别阈值。
向包含甜味剂的饮料中添加为处于或低于甜味识别阈值的浓度的甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM可以增加检测的蔗糖当量约1.0%至约5.0%,例如约1.0%,约1.5%,约2.0%,约2.5%,约3.0%,约3.5%,约4.0%,约4.5%或约5.0%。
下列实施例示例本发明用于制备高度纯化的目标甜菊糖苷的优选实施方案,特别是甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3和/或瑞鲍迪苷AM。可以理解,本发明不限于实施例中举出的材料,比例,条件和方法,它们仅为示例性的。
实施例
实施例1
生物催化方法中使用的改造的酶的蛋白质序列
SEQ ID 1:
>SuSy_At,变体PM1-54-2-E05(改造的蔗糖合酶;WT基因来源:拟南芥)
MANAERMITRVHSQRERLNETLVSERNEVLALLSRVEAKGKGILQQNQIIAEFEALPEQTRKKLEGGPFFDLLKSTQEAIVLPPWVALAVRPRPGVWEYLRVNLHALVVEELQPAEFLHFKEELVDGVKNGNFTLELDFEPFNASIPRPTLHKYIGNGVDFLNRHLSAKLFHDKESLLPLLDFLRLHSHQGKNLMLSEKIQNLNTLQHTLRKAEEYLAELKSETLYEEFEAKFEEIGLERGWGDNAERVLDMIRLLLDLLEAPDPSTLETFLGRVPMVFNVVILSPHGYFAQDNVLGYPDTGGQVVYILDQVRALEIEMLQRIKQQGLNIKPRILILTRLLPDAVGTTCGERLERVYDSEYCDILRVPFRTEKGIVRKWISRFEVWPYLETYTEDAAVELSKELNGKPDLIIGNYSDGNLVASLLAHKLGVTQCTIAHALEKTKYPDSDIYWKKLDDKYHFSCQFTADIFAMNHTDFIITSTFQEIAGSKETVGQYESHTAFTLPGLYRVVHGIDVFDPKFNIVSPGADMSIYFPYTEEKRRLTKFHSEIEELLYSDVENDEHLCVLKDKKKPILFTMARLDRVKNLSGLVEWYGKNTRLRELVNLVVVGGDRRKESKDNEEKAEMKKMYDLIEEYKLNGQFRWISSQMDRVRNGELYRYICDTKGAFVQPALYEAFGLTVVEAMTCGLPTFATCKGGPAEIIVHGKSGFHIDPYHGDQAADLLADFFTKCKEDPSHWDEISKGGLQRIEEKYTWQIYSQRLLTLTGVYGFWKHVSNLDRLEHRRYLEMFYALKYRPLAQAVPLAQDD
SEQ ID 2:
>UGTSl2变体0234(改造的葡糖基转移酶;WT基因来源:番茄)
MATNLRVLMFPWLAYGHISPFLNIAKQLADRGFLIYLCSTRINLESIIKKIPEKYADSIHLIELQLPELPELPPHYHTTNGLPPHLNPTLHKALKMSKPNFSRILQNLKPDLLIYDVLQPWAEHVANEQGIPAGKLLVSCAAVFSYFFSFRKNPGVEFPFPAIHLPEVEKVKIREILAKEPEEGGRLDEGNKQMMLMCTSRTIEAKYIDYCTELCNWKVVPVGPPFQDLITNDADNKELIDWLGTKPENSTVFVSFGSEYFLSKEDMEEIAFALEASNVNFIWVVRFPKGEERNLEDALPEGFLERIGERGRVLDKFAPQPRILNHPSTGGFISHCGWNSVMESIDFGVPIIAMPIHNDQPINAKLMVELGVAVEIVRDDDGKIHRGEIAEALKSVVTGETGEILRAKVREISKNLKSIRDEEMDAVAEELIQLCRNSNKSK
SEQ ID 3:
>UGT76G1变体0042(改造的葡糖基转移酶;WT基因来源:甜叶菊)
MENKTETTVRRRRRIILFPVPFQGHINPILQLANVLYSKGFAITILHTNFNKPKTSNYPHFTFRFILDNDPQDERISNLPTHGPLAGMRIPIINEHGADELRRELELLMLASEEDEEVSCLITDALWYFAQDVADSLNLRRLVLMTSSLFNFHAHVSLPQFDELGYLDPDDKTRLEEQASGFPMLKVKDIKSAYSNWQIGKEILGKMIKQTKASSGVIWNSFKELEESELETVIREIPAPSFLIPLPKHLTASSSSLLDHDRTVFEWLDQQAPSSVLYVSFGSTSEVDEKDFLEIARGLVDSGQSFLWVVRPGFVKGSTWVEPLPDGFLGERGKIVKWVPQQEVLAHPAIGAFWTHSGWNSTLESVCEGVPMIFSSFGGDQPLNARYMSDVLRVGVYLENGWERGEVVNAIRRVMVDEEGEYIRQNARVLKQKADVSLMKGGSSYESLESLVSYISSL
实施例2
SEQ ID 1的SuSy_At变体的表达和配制
将编码SEQ ID 1(实施例1)的SuSy_At变体的基因克隆到表达载体pLE1A17(pRSF-1b的衍生物,Novagen)中。将所得质粒用于转化大肠杆菌BL21(DE3)细胞。
在37℃下在补充有卡那霉素(50mg/l)的ZYM505培养基(F.William Studier,Protein Expression and Purification 41(2005)207-234)中培养细胞。IPTG(0.2mM)在对数期诱导基因表达,并在30℃和200rpm下进行16-18小时。
通过离心(3220xg,20min,4℃)收获细胞,并用细胞裂解缓冲液(100mM Tris-HClpH7.0;2mM MgCl2,DNA核酸酶20U/mL,溶菌酶0.5mg/mL)重悬为200的光密度(在600nm(OD600)处测量的)。然后通过超声处理破坏细胞,并通过离心(18000xg 40min,4℃)将粗提物与细胞碎片分离。通过0.2μm过滤器过滤将上清液灭菌,并用蒸馏水以50:50稀释,得到酶活性制剂。
对于SuSy_At的酶活性制剂,如下定义单位活性:1mU SuSy_At在1分钟内将1nmol的蔗糖转化为果糖。该测定的反应条件是30℃,50mM磷酸钾缓冲液pH7.0,t0下的400mM蔗糖,3mM MgCl2和15mM尿苷二磷酸(UDP)。
实施例3
SEQ ID 2的UGTSl2变体的表达和配制
将编码SEQ ID 2(实施例1)的UGTSl2变体的基因克隆到表达载体pLE1A17(pRSF-1b的衍生物,Novagen)中。将所得质粒用于转化大肠杆菌BL21(DE3)细胞。
在37℃下在补充有卡那霉素(50mg/l)的ZYM505培养基(F.William Studier,Protein Expression and Purification 41(2005)207-234)中培养细胞。用IPTG(0.1mM)在对数期诱导基因表达,并在30℃和200rpm下进行16-18小时。
通过离心(3220xg,20min,4℃)收获细胞,并用细胞裂解缓冲液(100mM Tris-HClpH 7.0;2mM MgCl2,DNA核酸酶20U/mL,溶菌酶0.5mg/mL)重悬至200的光密度(在600nm处测量的(OD600))。然后通过超声处理破坏细胞,并通过离心(18000xg 40min,4℃)将粗提物与细胞碎片分离。通过0.2μm过滤器过滤将上清液灭菌,并用1M蔗糖溶液以50:50稀释,得到酶活性制剂。
对于UGTSl2的酶活性制剂,如下定义单位活性:1mU UGTSl2在1分钟内将1nmol的瑞鲍迪苷A(RebA)转化为瑞鲍迪苷D(Reb D)。该测定的反应条件是30℃,50mM磷酸钾缓冲液pH7.0,t0下的10mM的RebA,500mM蔗糖3mM MgCl2和0.25mM尿苷二磷酸(UDP)和3U/mL的SuSy_At。
实施例4
SEQ ID 3的UGT76G1变体的表达和配制
将编码SEQ ID 3(实施例1)的UGT76G1变体的基因克隆到表达载体pLE1A17(pRSF-1b的衍生物,Novagen)中。将所得质粒用于转化大肠杆菌BL21(DE3)细胞。
在37℃下在补充有卡那霉素(50mg/l)的ZYM505培养基(F.William Studier,Protein Expression and Purification 41(2005)207-234)中培养细胞。用IPTG(0.1mM)在对数期诱导基因表达,并在30℃和200rpm下进行16-18小时。
通过离心(3220xg,20min,4℃)收获细胞,并用细胞裂解缓冲液(100mM Tris-HClpH 7.0;2mM MgCl2,DNA核酸酶20U/mL,溶菌酶0.5mg/mL)重悬至200的光密度(在600nm处测量的(OD600))。然后通过超声处理破坏细胞,并通过离心(18000xg 40min,4℃)将粗提物与细胞碎片分离。通过0.2μm过滤器过滤将上清液灭菌,并用1M蔗糖溶液以50:50稀释,得到酶活性制剂。
对于UGT76G1的酶活性制剂,如下定义单位活性:1mU UGT76G1在1分钟内将1nmol的瑞鲍迪苷D(Reb D)转化为瑞鲍迪苷M(Reb M)。该测定的反应条件是30℃,50mM磷酸钾缓冲液pH 7.0,t0下的10mM的RebA,500mM蔗糖,3mM MgCl2和0.25mM尿苷二磷酸(UDP)和3U/mL的SuSy_At。
实施例5
单罐反应中由甜菊苷合成瑞鲍迪苷AM,同时添加UGTSl2,SuSy_At和UGT76G1
在单罐反应中使用3种酶(参见实施例1,2,3和4)直接由甜菊苷合成瑞鲍迪苷AM(reb AM)(参见图3):UGTSl2(SEQ ID 2的变体),SuSy_At-(SEQ ID 1的变体)和UGT76G1(SEQ ID 3的变体)。最终反应溶液包含105U/L UGTSl2,405U/L SuSy_At,3U/L UGT76G1,5mM甜菊苷,0.25mM尿苷二磷酸(UDP),1M蔗糖,4mM MgCl2和磷酸钾缓冲液(pH 6.6)。首先,将207mL蒸馏水与0.24g MgCl2·6H2O,103g蔗糖,9.9mL 1.5M磷酸钾缓冲液(pH 6.6)和15g甜菊苷混合。在溶解所述组分后,将温度调节至45℃,加入UGTSl2,SuSy_At,UGT76G1和39mgUDP。将该反应混合物在45℃摇瓶中温育24hr。在8小时和18小时再加入39mg UDP。在几个时间点通过HPLC分析reb AM,reb E,甜菊苷,reb M,reb B,甜菊双糖苷和reb I的含量。
为了进行分析,通过用17%H3PO4将反应混合物调节至pH5.5使生物转化样品失活,然后煮沸10分钟。过滤所得样品,将滤液稀释10倍,用作HPLC分析样品。在Agilent HP1200HPLC系统上进行HPLC分析,该系统由泵,柱恒温器,自动进样器,能够背景校正的UV检测器和数据采集系统组成。使用Agilent Poroshell 120SB-C18,4.6mmx150mm,2.7μm在40℃时分离分析物。流动相由两种预混物组成:
-包含75%10mM磷酸缓冲液(pH2.6)和25%乙腈的预混物1;和
-包含68%10mM磷酸缓冲液(pH2.6)和32%乙腈的预混物2。
洗脱梯度从预混物1开始,在12.5分钟时变为预混物2至50%,在13分钟时变为预混物2至100%。总运行时间为45分钟。将柱温维持在40℃。进样量为5μL。在210nm通过UV检测到瑞鲍迪苷种类。
表3显示每个时间点将甜菊苷转化为已识别的瑞鲍迪苷种类(面积百分比)的过程。图5和图6分别显示了甜菊苷和反应混合物在24小时时的色谱图。本领域技术人员将理解,保留时间有时会随溶剂和/或设备的变化而变化。
表3
甜菊苷生物转化为reb AM
实施例6
单罐反应中由瑞鲍迪苷E合成瑞鲍迪苷AM,同时添加SuSy_At和UGT76G1
在单罐反应中使用2种酶(参见实施例1,2和4)直接由瑞鲍迪苷E(reb E)合成瑞鲍迪苷AM(reb AM)(参见图4):SuSy_At-(SEQ ID 1的变体)和UGT76G1(SEQ ID 3的变体)。最终反应溶液包含405U/L SuSy_At,3U/L UGT76G1,5mM reb E,0.25mM尿苷二磷酸(UDP),1M蔗糖,4mM MgCl2·6H2O和磷酸钾缓冲液(pH 6.6)。首先,将37mL蒸馏水与40.3mg MgCl2,17.12g蔗糖,1.65mL 1.5M磷酸钾缓冲液(pH 6.6)和5.04g reb E混合。在溶解所述组分后,将温度调节至45℃,加入SuSy_At,UGT76G1和6.5mg UDP。将该反应混合物在45℃摇瓶中温育24hr。在8小时和18小时再加入6.5mg UDP。在几个时间点通过HPLC分析reb AM,reb E,甜菊苷,reb A,reb M,reb B和甜菊双糖苷的含量。
为了进行分析,通过用17%H3PO4将反应混合物调节至pH5.5使生物转化样品失活,然后煮沸10分钟。过滤所得样品,将滤液稀释10倍,用作HPLC分析样品。在Agilent HP 1200HPLC系统上进行HPLC分析,该系统由泵,柱恒温器,自动进样器,能够背景校正的UV检测器和数据采集系统组成。使用Agilent Poroshell 120SB-C18,4.6mmx150mm,2.7μm在40℃时分离分析物。流动相由两种预混物组成:
-包含75%10mM磷酸缓冲液(pH2.6)和25%乙腈的预混物1;和
-包含68%10mM磷酸缓冲液(pH2.6)和32%乙腈的预混物2。
洗脱梯度从预混物1开始,在12.5分钟时变为预混物2至50%,在13分钟时变为预混物2至100%。总运行时间为45分钟。将柱温维持在40℃。进样量为5μL。在210nm通过UV检测到瑞鲍迪苷种类。
表4显示每个时间点将瑞鲍迪苷E转化为已识别的瑞鲍迪苷种类(面积百分比)的过程。图7和图8分别显示了瑞鲍迪苷E和反应混合物在24小时时的色谱图。本领域技术人员将理解,保留时间有时会随溶剂和/或设备的变化而变化。
表4
reb E生物转化为reb AM
实施例7
瑞鲍迪苷AM的纯化
将实施例5的反应混合物(24hr后),用H3PO4将pH调节至pH5.5使其失活,然后煮沸10分钟。沸腾后,将反应混合物过滤并用RO水稀释至5%固体含量。将稀释后的溶液通过装有YWD03大孔吸附树脂的1L柱子(Cangzhou Yuanwei,中国)。用5L 70%乙醇洗脱吸附的甜菊糖苷。将获得的洗脱液蒸发至干,得到16g的干粉,将其溶于80mL的70%甲醇中。将该溶液在20℃下结晶3天。将晶体通过过滤分离,并在80℃的真空烘箱中干燥18小时,得到10.4g具有95.92%纯度的纯reb AM晶体,通过HPLC测定法测定。reb AM的色谱图如图9所示。本领域技术人员将理解,保留时间有时会随溶剂和/或设备的变化而变化。
实施例8
瑞鲍迪苷AM的结构阐述
使用Bruker 500MHz光谱仪进行NMR实验,其中将样品溶于吡啶-d5。观察到来自在δC 123.5,135.5,149.9ppm和δH 7.19,7.55,8.71ppm的吡啶-d5的信号与来自样品的信号。
在吡啶-d5中记录的瑞鲍迪苷AM的1H-NMR光谱显示了样品的极佳质量(参见图10)。HSQC(参见图11)显示具有与C-15长范围偶联的糖区中存在外-亚甲基,这可在H,H-COSY中观察到(图12)。通过HMBC(图13)检测到其他季碳(C-13,C-16和C-19)的深场信号。HSQC,HMBC和H,H-COSY中信号的相关性揭示了具有以下苷元结构的甜菊糖苷的存在:
HSQC和HMBC信号的相关性揭示了五个端基异构信号。端基异构质子的耦合常数为约8Hz,并且其糖键的宽信号使得能够将这5种糖鉴定为β-D-吡喃葡萄糖苷。
端基异构质子与HSQC和HMBC结合的观察表明糖键和与苷元的相关性。通过使用HSQC-TOCSY(图14)和HSQC的组合确定了糖序列的指定。
上面的NMR实验用于指定质子和碳的化学位移,主要的偶合常数和主要的HMBC相关性(参见表5)。
表5
瑞鲍迪苷AM的化学位移
表5(续)
瑞鲍迪苷AM的化学位移
所有NMR数据的相关性显示具有与甜菊糖苷元相连的五个β-D-吡喃葡萄糖的瑞鲍迪苷AM,如以下化学结构所示:
瑞鲍迪苷AM的化学式为C50H80O28,对应于计算得出的单同位素分子量1128.5。对于LCMS分析,将瑞鲍迪苷AM溶解在甲醇中,并使用Shimadzu Nexera 2020UFLC LCMS仪器在Cortecs UPLC C181.6μm,50x2.1mm柱上进行分析。所观察到的LCMS(负ESI模式)结果为1127.3(分别参见图15a和图15b),与瑞鲍迪苷AM一致并且对应于离子(M-H)-。
序列表
<110> PureCircle USA Inc.
<120> 高纯度甜菊糖苷
<130> 39227-77WO
<160> 3
<170> PatentIn version 3.5
<210> 1
<211> 808
<212> PRT
<213> 拟南芥
<400> 1
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35 40 45
Ile Ile Ala Glu Phe Glu Ala Leu Pro Glu Gln Thr Arg Lys Lys Leu
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Lys Asn Gly Asn Phe Thr Leu Glu Leu Asp Phe Glu Pro Phe Asn Ala
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Ser Ile Pro Arg Pro Thr Leu His Lys Tyr Ile Gly Asn Gly Val Asp
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Val Trp Pro Tyr Leu Glu Thr Tyr Thr Glu Asp Ala Ala Val Glu Leu
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Ser Lys Glu Leu Asn Gly Lys Pro Asp Leu Ile Ile Gly Asn Tyr Ser
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Asp Gly Asn Leu Val Ala Ser Leu Leu Ala His Lys Leu Gly Val Thr
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Gln Cys Thr Ile Ala His Ala Leu Glu Lys Thr Lys Tyr Pro Asp Ser
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Asp Ile Tyr Trp Lys Lys Leu Asp Asp Lys Tyr His Phe Ser Cys Gln
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Phe Thr Ala Asp Ile Phe Ala Met Asn His Thr Asp Phe Ile Ile Thr
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Asp Met Ser Ile Tyr Phe Pro Tyr Thr Glu Glu Lys Arg Arg Leu Thr
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Asp Glu His Leu Cys Val Leu Lys Asp Lys Lys Lys Pro Ile Leu Phe
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Thr Met Ala Arg Leu Asp Arg Val Lys Asn Leu Ser Gly Leu Val Glu
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Trp Tyr Gly Lys Asn Thr Arg Leu Arg Glu Leu Val Asn Leu Val Val
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Val Gly Gly Asp Arg Arg Lys Glu Ser Lys Asp Asn Glu Glu Lys Ala
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Glu Met Lys Lys Met Tyr Asp Leu Ile Glu Glu Tyr Lys Leu Asn Gly
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Gln Phe Arg Trp Ile Ser Ser Gln Met Asp Arg Val Arg Asn Gly Glu
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Leu Tyr Arg Tyr Ile Cys Asp Thr Lys Gly Ala Phe Val Gln Pro Ala
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Leu Tyr Glu Ala Phe Gly Leu Thr Val Val Glu Ala Met Thr Cys Gly
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Leu Pro Thr Phe Ala Thr Cys Lys Gly Gly Pro Ala Glu Ile Ile Val
690 695 700
His Gly Lys Ser Gly Phe His Ile Asp Pro Tyr His Gly Asp Gln Ala
705 710 715 720
Ala Asp Leu Leu Ala Asp Phe Phe Thr Lys Cys Lys Glu Asp Pro Ser
725 730 735
His Trp Asp Glu Ile Ser Lys Gly Gly Leu Gln Arg Ile Glu Glu Lys
740 745 750
Tyr Thr Trp Gln Ile Tyr Ser Gln Arg Leu Leu Thr Leu Thr Gly Val
755 760 765
Tyr Gly Phe Trp Lys His Val Ser Asn Leu Asp Arg Leu Glu His Arg
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Arg Tyr Leu Glu Met Phe Tyr Ala Leu Lys Tyr Arg Pro Leu Ala Gln
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Ala Val Pro Leu Ala Gln Asp Asp
805
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<213> 番茄
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Met Ala Thr Asn Leu Arg Val Leu Met Phe Pro Trp Leu Ala Tyr Gly
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His Ile Ser Pro Phe Leu Asn Ile Ala Lys Gln Leu Ala Asp Arg Gly
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Gln Leu Pro Glu Leu Pro Glu Leu Pro Pro His Tyr His Thr Thr Asn
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Gly Leu Pro Pro His Leu Asn Pro Thr Leu His Lys Ala Leu Lys Met
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Ser Lys Pro Asn Phe Ser Arg Ile Leu Gln Asn Leu Lys Pro Asp Leu
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Pro Ala Ile His Leu Pro Glu Val Glu Lys Val Lys Ile Arg Glu Ile
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<213> 甜叶菊
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Phe Ala Gln Asp Val Ala Asp Ser Leu Asn Leu Arg Arg Leu Val Leu
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Met Thr Ser Ser Leu Phe Asn Phe His Ala His Val Ser Leu Pro Gln
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Phe Asp Glu Leu Gly Tyr Leu Asp Pro Asp Asp Lys Thr Arg Leu Glu
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Glu Gln Ala Ser Gly Phe Pro Met Leu Lys Val Lys Asp Ile Lys Ser
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Ala Tyr Ser Asn Trp Gln Ile Gly Lys Glu Ile Leu Gly Lys Met Ile
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Ala Arg Tyr Met Ser Asp Val Leu Arg Val Gly Val Tyr Leu Glu Asn
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Gly Trp Glu Arg Gly Glu Val Val Asn Ala Ile Arg Arg Val Met Val
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Asp Glu Glu Gly Glu Tyr Ile Arg Gln Asn Ala Arg Val Leu Lys Gln
420 425 430
Lys Ala Asp Val Ser Leu Met Lys Gly Gly Ser Ser Tyr Glu Ser Leu
435 440 445
Glu Ser Leu Val Ser Tyr Ile Ser Ser Leu
450 455
Claims (14)
2.用于生产高度纯化的权利要求1的瑞鲍迪苷AM的方法,包括下列步骤:
a.提供包含具有至少一个碳原子的有机化合物的起始组合物;
b.提供选自酶制剂、细胞或微生物的生物催化剂;所述生物催化剂包含至少一种能够将所述起始组合物转化为瑞鲍迪苷AM的酶;
c.使所述生物催化剂与含有所述起始组合物的介质接触,产生包含瑞鲍迪苷AM的介质。
3.权利要求2的方法,还包括下列步骤:
d.从所述介质中分离瑞鲍迪苷AM,提供高度纯化的瑞鲍迪苷AM组合物。
4.权利要求2的方法,其中所述起始组合物选自甜菊醇,甜菊单糖苷,甜菊单糖苷A,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜茶苷,甜菊苷,甜菊苷A(瑞鲍迪苷KA),甜菊苷B,甜菊苷C,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3,其他甜菊糖苷,多元醇,糖类及其组合。
5.权利要求2的方法,其中所述微生物选自大肠杆菌(E.coli),酵母属(Saccharomycessp.),曲霉属(Aspergillus sp.),毕赤酵母属(Pichia sp.),芽孢杆菌属(Bacillus sp.)和耶罗威亚酵母属(Yarrowia sp.)。
6.权利要求2的方法,其中所述酶选自:甜菊醇生物合成酶,UDP葡糖基转移酶,UDP葡萄糖再循环酶,甲羟戊酸(MVA)途径酶,2-C-甲基-D-赤藓糖醇-4-磷酸途径(MEP/DOXP)酶,香叶基香叶基二磷酸合酶,柯巴基二磷酸合酶,贝壳杉烯合酶,贝壳杉烯氧化酶,贝壳杉烯酸13-羟化酶(KAH),甜菊醇合成酶,脱氧木酮糖5-磷酸合酶(DXS),D-1-脱氧木酮糖5-磷酸还原异构酶(DXR),4-二磷酸胞嘧啶基-2-C-甲基-D-赤藓糖醇合酶(CMS),4-二磷酸胞嘧啶基-2-C-甲基-D-赤藓糖醇激酶(CMK),4-二磷酸胞嘧啶基-2-C-甲基-D-赤藓糖醇2,4-环二磷酸合酶(MCS),l-羟基-2-甲基-2(E)-丁烯基4-二磷酸合酶(HDS),l-羟基-2-甲基-2(E)-丁烯基4-二磷酸还原酶(HDR),乙酰乙酰基-CoA硫解酶,截短型HMG-CoA还原酶,甲羟戊酸激酶,磷酸甲羟戊酸激酶,甲羟戊酸焦磷酸脱羧酶,细胞色素P450还原酶,UGT74G1,UGT85C2,UGT91D2,EUGT11,UGTSl2,UGT76G1或其具有>85%氨基酸序列同一性,>86%氨基酸序列同一性,>87%氨基酸序列同一性,>88%氨基酸序列同一性,>89%氨基酸序列同一性,>90%氨基酸序列同一性,>91%氨基酸序列同一性,>92%氨基酸序列同一性,>93%氨基酸序列同一性,>94%氨基酸序列同一性,>95%氨基酸序列同一性,>96%氨基酸序列同一性,>97%氨基酸序列同一性,>98%氨基酸序列同一性,>99%氨基酸序列同一性的突变变体;及其组合。
7.权利要求3的方法,其中高度纯化的瑞鲍迪苷AM组合物中瑞鲍迪苷AM含量基于干重大于约95%重量。
8.消费产品,包含权利要求1的瑞鲍迪苷AM,其中所述产品选自食品,饮料,药物组合物,烟草产品,营养保健品组合物,口腔卫生组合物和化妆品组合物。
9.权利要求8的消费产品,还包含至少一种添加剂,其选自糖类,多元醇,氨基酸及其相应的盐,聚氨基酸及其相应的盐,糖酸及其相应的盐,核苷酸,有机酸,无机酸,有机盐,包括有机酸盐和有机碱盐,无机盐,苦味化合物,咖啡碱,香料和调味剂成分,收敛化合物,蛋白质或蛋白水解产物,表面活性剂,乳化剂,类黄酮,醇,聚合物及其组合。
10.权利要求8的消费产品,还包含至少一种功能性成分,其选自皂苷,抗氧化剂,膳食纤维源,脂肪酸,维生素,葡糖胺,矿物质,防腐剂,水合剂,益生菌,益生元,体重处置剂,骨质疏松处置剂,植物雌激素,长链伯脂族饱和醇,植物甾醇及其组合。
11.权利要求8的消费产品,还包含选自如下的化合物:瑞鲍迪苷A,瑞鲍迪苷A2,瑞鲍迪苷A3,瑞鲍迪苷B,瑞鲍迪苷C,瑞鲍迪苷C2,瑞鲍迪苷D,瑞鲍迪苷D2,瑞鲍迪苷E,瑞鲍迪苷E2,瑞鲍迪苷E3,瑞鲍迪苷F,瑞鲍迪苷F2,瑞鲍迪苷F3,瑞鲍迪苷G,瑞鲍迪苷H,瑞鲍迪苷I,瑞鲍迪苷I2,瑞鲍迪苷I3,瑞鲍迪苷J,瑞鲍迪苷K,瑞鲍迪苷K2,瑞鲍迪苷KA,瑞鲍迪苷L,瑞鲍迪苷M,瑞鲍迪苷M2,瑞鲍迪苷N,瑞鲍迪苷O,瑞鲍迪苷O2,瑞鲍迪苷Q,瑞鲍迪苷Q2,瑞鲍迪苷Q3,瑞鲍迪苷R,瑞鲍迪苷S,瑞鲍迪苷T,瑞鲍迪苷T1,瑞鲍迪苷U,瑞鲍迪苷U2,瑞鲍迪苷V,瑞鲍迪苷W,瑞鲍迪苷W2,瑞鲍迪苷W3,瑞鲍迪苷Y,瑞鲍迪苷Z1,瑞鲍迪苷Z2,杜克苷A,杜克苷C,甜茶苷,甜菊双糖苷,甜菊双糖苷A,甜菊双糖苷B,甜菊单糖苷,甜菊单糖苷A,甜菊苷,甜菊苷A,甜菊苷B,甜菊苷C,甜菊苷D,甜菊苷E,甜菊苷E2,甜菊苷F,NSF-02,罗汉果苷V,罗汉果,阿洛酮糖,D-阿洛糖,D-塔格糖,赤藓糖醇,甜味蛋白,新橙皮苷二氢查耳酮,甘草酸及其盐,奇异果甜蛋白,紫苏葶,皮尔南甘素,无患子倍半萜苷,白元参苷,糙苏苷-I,二甲基-六氢芴-二羧酸,相思子三萜苷,巴西甘草甜素,肉质雪胆皂苷,青钱柳苷,裂环达玛烷型三萜苷,聚波朵苷A,巴西红木素,贺兰甜精,菲络杜辛,菝葜苷,根皮苷,三叶苷,二氢黄酮醇,二氢槲皮素-3-乙酸酯,新落新妇苷,反式-肉桂醛,莫纳甜及其盐,修藤精A,苏木素,莫内甜蛋白,水龙骨甜素,蝶卡苷A,蝶卡苷B,马槟榔甜蛋白,培它丁,改味糖蛋白,仙茅甜蛋白,新仙茅甜蛋白,绿原酸,洋蓟素,赛门苷,三氯蔗糖,乙酰磺胺酸钾,阿斯巴甜,阿力甜,糖精,环己氨磺酸盐,纽甜,甘素,suosan advantame,匙羹藤酸,勿甜素,ziziphin,降甜香精,谷氨酸盐,天冬氨酸,甘氨酸,丙氨酸,苏氨酸,脯氨酸,丝氨酸,赖氨酸,色氨酸,麦芽糖醇,甘露糖醇,山梨糖醇,乳糖醇,木糖醇,肌醇,异麦芽酮糖醇,丙二醇,甘油,苏糖醇,半乳糖醇,氢化异麦芽酮糖,还原异麦芽寡糖,还原木寡糖,还原龙胆寡糖,还原麦芽糖浆,还原葡萄糖浆,氢化淀粉水解产物,聚葡糖醇,糖醇,L-糖,L-山梨糖,L-阿拉伯糖,海藻糖,半乳糖,鼠李糖,各种环糊精,环寡糖,各种类型的麦芽糖糊精,葡聚糖,蔗糖,葡萄糖,核酮糖,果糖,苏阿糖,木糖,来苏糖,阿卓糖,甘露糖,艾杜糖,乳糖,麦芽糖,转化糖,异海藻糖,新海藻糖,异麦芽酮糖,赤藓糖,脱氧核糖,古洛糖,塔罗糖,赤藓酮糖,木酮糖,纤维二糖,支链淀粉,葡糖胺,甘露糖胺,葡糖醛酸,葡糖酸,葡糖酸内酯,阿比可糖,半乳糖胺,甜菜寡糖,异麦芽寡糖(异麦芽糖,异麦芽三糖,潘糖等),木寡糖(木三糖,木二糖等),木糖终止的寡糖,龙胆寡糖(龙胆二糖,龙胆三糖,龙胆四糖等),黑曲霉寡糖,帕拉金糖寡糖,果寡糖(蔗果三糖,蔗果四糖等),麦芽四糖醇,麦芽三糖醇,麦芽寡糖(麦芽三糖,麦芽四糖,麦芽五糖,麦芽六糖,麦芽七糖等),淀粉,菊糖,菊寡糖,乳果糖,蜜二糖,棉子糖,异构化液体糖例如高果糖玉米糖浆,偶联糖,大豆寡糖,D-阿洛酮糖,D-核糖,L-葡萄糖,L-岩藻糖,D-松二糖,D-明串珠菌二糖。
12.用于改良消费品的风味的方法,包括下列步骤:
a.提供消费品;和
b.添加包含权利要求1的瑞鲍迪苷AM的具有改良特性的调味剂,
其中瑞鲍迪苷AM以处于或低于所述具有改良特性的调味剂的检测阈值的浓度存在于消费品中。
13.权利要求12的方法,其中改良风味包括增强所述消费品的甜味。
14.用于抑制饮料或食品的发泡的方法,包括:
a.提供饮料或食品,和
b.添加包含权利要求1的瑞鲍迪苷AM的泡沫抑制剂。
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BR (1) | BR112020019012B1 (zh) |
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WO2023083163A1 (en) * | 2021-11-12 | 2023-05-19 | Epc Natural Products Co., Ltd. | Sweetener and flavor composition comprising glycosylated high purity steviol glycosides |
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CA3078545A1 (en) | 2017-10-06 | 2019-04-11 | Cargill, Incorporated | Stabilized steviol glycoside compositions and uses thereof |
GB201805576D0 (en) * | 2018-04-04 | 2018-05-16 | Optibiotix Ltd | Sweeteners and methods of production thereof |
CN113727614B (zh) | 2019-04-06 | 2024-06-04 | 嘉吉公司 | 感官改性剂 |
WO2020236684A1 (en) * | 2019-05-17 | 2020-11-26 | Purecircle Usa Inc. | Stevia flavor compositions |
CN112553175B (zh) * | 2019-09-26 | 2023-04-07 | 中国科学院分子植物科学卓越创新中心 | 糖基转移酶ugt76g1突变体的制备及其应用 |
MX2022013915A (es) * | 2020-05-07 | 2023-02-22 | Coca Cola Co | Bebidas que comprenden rebaudiosido am y rebaudiosido m con sabor mejorado. |
EP4271205A1 (en) * | 2020-12-30 | 2023-11-08 | CORN Products Development Inc. | Beverages comprising reb a and steviol glycosides |
EP4363431A1 (en) * | 2021-06-29 | 2024-05-08 | Purecircle SDN BHD | High-purity steviol glycosides |
EP4395568A1 (en) | 2021-09-01 | 2024-07-10 | The Coca-Cola Company | Methods and compositions comprising caffeine and/or a derivative thereof and a polyphenol |
CN114886801B (zh) * | 2022-05-19 | 2023-06-13 | 浙江湃肽生物股份有限公司 | 用于抗炎舒敏修复的多肽组合物及其制备方法和应用 |
WO2024026450A1 (en) * | 2022-07-29 | 2024-02-01 | Corn Products Development, Inc. | Flavor modifying composition |
WO2024081959A2 (en) | 2022-10-14 | 2024-04-18 | The Coca-Cola Company | Methods and compositions for improving cognitive and mood functions |
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- 2018-04-10 WO PCT/US2018/026920 patent/WO2019177634A1/en active Application Filing
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BR112020019012A2 (pt) | 2020-12-29 |
KR20200133250A (ko) | 2020-11-26 |
EP3764810A1 (en) | 2021-01-20 |
WO2019177634A1 (en) | 2019-09-19 |
BR112020019012B1 (pt) | 2023-11-28 |
MX2020009625A (es) | 2021-02-16 |
JP2023145440A (ja) | 2023-10-11 |
CA3094154A1 (en) | 2019-09-19 |
US20210095322A1 (en) | 2021-04-01 |
AU2018413277B2 (en) | 2024-07-11 |
AU2018413277A1 (en) | 2020-10-08 |
EP3764810A4 (en) | 2021-10-20 |
JP2021527622A (ja) | 2021-10-14 |
US20210107933A1 (en) | 2021-04-15 |
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