CN115974742A - 温和条件下dmshb的制备与结构表征方法 - Google Patents
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Abstract
本发明涉及一种温和条件下DMSHB的制备与结构表征方法,属于有机合成技术领域,本发明通过解析DMSHB的结构特征,以4‑甲硫基‑2‑羟基丁酸(MTHB)为先导化合物,采用亲核加成方法,对MTHB进行结构改造和化学修饰,最终制备了目标化合物DMSHB。本发明还公开了实现DMSHB结构表征的方法。与其他制备方法相比,本发明采用的合成方法有效,制备工艺简单,结构鉴定方法准确可行。
Description
技术领域
本发明属于有机合成技术领域,具体涉及一种温和条件下4-二甲基巯基-2-羟基丁酸(DMSHB)的制备与结构表征方法。
背景技术
二甲基巯基丙酸内盐(DMSP:(CH3)2SCH2CH2COOH)是海洋浮游植物合成的一种天然水产诱食剂,具有重要的经济价值。DMSP在自然界中广泛存在,不仅广泛存在海藻体内,也存在于野生的鱼虾体中。作为水产领域的重要诱食剂,DMSP的诱食剂机理已被阐明,其极易溶于水,并在水中迅速扩散,从而刺激水产动物的嗅觉神经。同时,水产动物体内具有感受(CH3)2S-基团的化学感受器,而(CH3)2S-基团是DMSP的特征基团。
DMSHB是DMSP生物合成的关键前体物质。一些浮游植物体内添加DMSHB后,经氧化脱羧过程可合成DMSP,这就为DMSP生产提供了有利的条件。目前市面上常见的诱食剂为DMSP的替代品—二甲基-β-丙酸噻亭(DMPT),由二甲基硫醚和3-溴丙酸(或3-氯丙酸)反应得到的,其生产成本高昂,严重制约了它的生产和应用。生物合成技术克服了上述化学合成法的不利条件,为DMSP规模化应用提供了很好的解决方案。然而,由于缺乏DMSP合成关键前体物DMSHB,且目前关于DMSHB制备的研究很少,因此无法有效利用DMSHB来实现DMSP生物合成,使得DMSP规模化制备的生产方案具有明显的不可操作性。因此,本发明的实践应用有效解决了DMSP生物合成技术的难题,克服了制约其实现商业化应用的瓶颈。
发明内容
本发明的目的是提供一种温和条件下制备4-二甲基巯基-2-羟基丁酸(DMSHB)及结构表征的方法,所述方法以化合物2-羟基-4-(甲硫基)丁酸(MTHB)为先导化合物,经亲核加成反应、离子交换树脂层析和旋转蒸发,制备目标化合物的一种有机合成方法,同时也开发了利用质谱法和核磁共振氢谱法进行结构表征的方法。该发明解决了DMSHB制备和结构表征等难题,并为天然水产诱食剂DMSP的生物合成提供了可能。
为了实现上述目的,本发明提供了以下技术方案:
一种温和条件下4-二甲基巯基-2-羟基丁酸(DMSHB)的制备,所述方法包括以下步骤:
(1)将化合物MTHB溶于超纯水中,搅拌、静置,加入碘甲烷(CH3I),加热反应,得到中间体DMSHB碘化物或混合物;
(2)将所得中间体DMSHB碘化物或混合物洗脱,去除碘离子(I-),收集溶液,蒸发掉水分,得到目标化合物。
进一步的,所述步骤(1)中静置时间为1-2h,静置温度为室温。
进一步的,所述步骤(1)中的碘甲烷的添加量为1.0~5.0eq。
进一步的,所述步骤(1)中CH3I以缓慢的流速逐滴加入,温度为室温。
进一步的,所述步骤(1)中加热方式为油浴,反应温度为40-50℃,反应时间为3-5h。
进一步的,所述步骤(2)中洗脱液为超纯水,洗脱次数为3次,层析柱为碱性离子交换树脂柱。
进一步的,所述步骤(2)中蒸发掉水分采用减压旋蒸方法,温度为30-40℃,或者采用冷冻干燥方法。
进一步的,所述步骤(2)中液相色谱柱为AgilentZORBAX Eclipse XDB-C18(4.6×250mm,粒径5μM),洗脱液为不同比例的0.1%甲酸水和0.1%甲酸乙腈溶液。
本发明还提供对目标化合物进行结构表征的方法,所述方法为利用液相色谱联合质谱仪(LC-MS)和核磁共振氢谱(1HNMR)对目标化合物进行表征,
进一步,其中质谱的离子源为API-ESI,毛细管电压3000V,雾化器压力35psi,干燥器温度350℃,扫描方式为全扫描模式,m/z扫描范围为100-1000,雾化气体流量9l/min。
进一步,所述待进行结构表征的目标化合物分别加入0.5mL DMSO和D2O中复溶,4℃、12000rpm离心3min后置于核磁管中。
本发明与现有技术相比的有益效果为:
目前市场上无纯品DMSHB及相关衍生产品,本发明首次实现了以MTHB为反应原材料,通过亲核加成反应得到中间体DMSHB碘化物;中间体DMSHB碘化物经层析法脱除I-,减压旋蒸生成目标化合物DMSHB;并建立了DMSHB的高效、准确的检测方法。本发明利用上述技术合成的DMSHB,具有合成效率高、反应物纯度高、反应体系简单等优势,利用该技术和方法可以规模化生产高纯度DMSHB,从而为其产业化应用奠定坚实的基础。
附图说明
图1为本发明的DMSHB制备过程图。
图2为DMSHB的总离子流TIC色谱图色。
图3为DMSHB的EIMS图。
图4为MTHB的1H NMR谱图。
图5为DMSHB的1H NMR谱图。A:DMSHB的原始1H NMR谱图;B:1H NMR解析结果。
具体实施方式
下面结合具体实施例对本发明的技术方案做进一步详细的说明。
实施例1:DMSHB制备技术的建立
取Amberlite IRN78(Hydroxide form)碱性离子交换树脂置于玻璃柱中,用纯净水洗涤,直至洗涤液无色为止,待用。化合物2-羟基-4-(甲硫基)丁酸(MTHB)溶于纯水溶液中,于室温滴加1.0-5.0eq碘甲烷(CH3I)均可,本实施例滴加的碘甲烷为1.0eq,加毕,置于40-50℃的加热,加热方式通常采用油浴,易于控制温,也可以采用其它方式进行加热,反应3-5h。反应液冷却后,将其注入预先处理的碱性离子交换树脂柱中,用纯净水或超纯水洗脱,收集组分,获得DMSHB,制备过程的化学反应式如图1所示。
实施例2:DMSHB的LC-MS检测方法建立
收集样品进行冷冻真空干燥24-36h,直到水分完全除尽。将所得粗品用500μL超纯水复溶,利用液相色谱联合质谱仪(LC-MS)进行结构鉴定,色谱条件如下:液相色谱柱为Agilent ZORBAX Eclipse XDB-C18(4.6×250mm,粒径5μM)。溶剂:A为含0.1%甲酸水溶液,B为0.1%甲酸乙腈溶液。流速为0.9mL/min,梯度(溶剂A/B百分比)为t=0min,95%A,5%B;t=10min,95%A,5%B;t=15min,90%A,10%B。质谱条件:离子源为API-ESI,毛细管电压3000V,雾化器压力35psi,干燥器温度350℃,扫描方式为全扫描模式,m/z扫描范围为100-1000,雾化气体流量9l/min。进样量为10μL。结果如图2、图3所示。已知DMSHB的分子式为C6H13O3S,理论分子量为164.2。如图2所示,该化合物在保留时间2.732min处被检测到,对应正离子模式[M+H]+下质谱图中的离子峰m/z 165.1(图3)。因此,该化合物的分子量为164.1,与DMSHB的理论分子量(164.2)基本一致。
实施例3:DMSHB的1H NMR分析
准确称取5mg MTHB样品和5mg冷冻干燥的合成样品,分别加入0.5mL DMSO和D2O中复溶,4℃、12000rpm离心3min后置于核磁管中,采用JEOL ECP600MHz核磁共振波谱仪测定其一维(1H NMR)核磁共振氢谱。原料MTHB的1H NMR谱如图4所示。随后,对目标化合物进行了结构表征,氢谱结果如图5中的A、B所示。通过结构解析,DMSHB的1H NMR谱(5B)在δH2.80(6H,H-1)处有2个甲基信号,积分值6;2个亚甲基信号δH2.16(1H,H-3a)、δH2.19(1H,H-3b),δH3.27(2H,H-2),积分值分别1.08、1.04、2.04;1个次甲基信号δH4.07(1H,H-4),积分值0.99。1H NMR结果表明,目标化合物DMSHB结构清晰,纯度高,完全满足作为标准品的要求。
实施例4:DMSHB的实际应用实例
生物合成DMSP的前体物质为DMSHB,DMSHB制备对DMSP生物合成特别是水产饲料诱食剂的开发与替代有重要意义。首先DMSP生物合成需要系列酶的催化,其中负责MTHB转化为DMSHB的合成酶被认为是DMSP生物合成的限速酶,影响整条合成途径的总速度以及合成方向等。DMSHB制备工艺开发和检测方法建立,不仅有助于筛选催化DMSHB合成所必需的关键酶,以期实现DMSP的绿色制备;同时也从传统化工合成角度为DMSP制备提供了另一种可能性方案。
以上实施例仅用以说明本发明的技术方案,而非对其进行限制;尽管参照前述实施例对本发明进行了详细的说明,对于本领域的普通技术人员来说,依然可以对前述实施例所记载的技术方案进行修改,或者对其中部分技术特征进行等同替换;而这些修改或替换,并不使相应技术方案的本质脱离本发明所要求保护的技术方案的精神和范围。
Claims (10)
1.一种温和条件下4-二甲基巯基-2-羟基丁酸的制备方法,其特征在于,所述方法包括以下步骤:
(1)将化合物2-羟基-4-(甲硫基)丁酸溶于超纯水中,搅拌、静置,加入碘甲烷,加热反应,得到中间体4-二甲基巯基-2-羟基丁酸碘化物或混合物;
(2)将所得中间体4-二甲基巯基-2-羟基丁酸碘化物或混合物洗脱,去除碘离子,收集溶液,蒸发掉水分,得到目标化合物。
2.根据权利要求1所述的一种温和条件下4-二甲基巯基-2-羟基丁酸的制备方法,其特征在于,所述步骤(1)中静置时间为1-2h,静置温度为室温。
3.根据权利要求1所述的一种温和条件下4-二甲基巯基-2-羟基丁酸的制备方法,其特征在于,所述步骤(1)中的碘甲烷的添加量为1.0~5.0eq。
4.根据权利要求1所述的一种温和条件下4-二甲基巯基-2-羟基丁酸的制备方法,其特征在于,所述步骤(1)中CH3I以缓慢的流速逐滴加入,温度为室温。
5.根据权利要求1所述的一种温和条件下4-二甲基巯基-2-羟基丁酸的制备方法,其特征在于,所述步骤(1)中加热方式为油浴,反应温度为40-50℃,反应时间为3-5h。
6.根据权利要求1所述的一种温和条件下4-二甲基巯基-2-羟基丁酸的制备方法,其特征在于,所述步骤(2)中洗脱液为超纯水,洗脱次数为3次,层析柱为碱性离子交换树脂柱。
7.根据权利要求1所述的一种温和条件下4-二甲基巯基-2-羟基丁酸的制备方法,其特征在于,所述步骤(2)中蒸发掉水分采用减压旋蒸方法,温度为30-40℃,或者采用冷冻干燥方法。
8.根据权利要求1所述的一种温和条件下4-二甲基巯基-2-羟基丁酸的制备方法,其特征在于,所述步骤(2)中液相色谱柱为Agilent ZORBAX Eclipse XDB-C184.6×250mm,粒径5μM,洗脱液为不同比例的0.1%甲酸水和0.1%甲酸乙腈溶液。
9.权利要求1-8任何一项所述方法制备的目标化合物进行结构表征的方法,其特征在于,所述方法为利用液相色谱联合质谱仪和核磁共振氢谱对目标化合物进行表征。
10.根据权利要求9所述的方法,其特征在于,质谱的离子源为API-ESI,毛细管电压3000V,雾化器压力35psi,干燥器温度350℃,扫描方式为全扫描模式,m/z扫描范围为100-1000,雾化气体流量9l/min;
所述待进行结构表征的目标化合物分别加入0.5mL DMSO和D2O中复溶,4℃、12000rpm离心3min后置于核磁管中。
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Publication number | Priority date | Publication date | Assignee | Title |
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US3763230A (en) * | 1971-08-03 | 1973-10-02 | Degussa | Sulfonium compounds of alpha-hydroxy-ypsilon-alkylmercaptobutyric acid |
US20130204016A1 (en) * | 2010-10-15 | 2013-08-08 | Adisseo France S.A.S. | Method for preparing 2-hydroxybutyrolactone |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3763230A (en) * | 1971-08-03 | 1973-10-02 | Degussa | Sulfonium compounds of alpha-hydroxy-ypsilon-alkylmercaptobutyric acid |
US20130204016A1 (en) * | 2010-10-15 | 2013-08-08 | Adisseo France S.A.S. | Method for preparing 2-hydroxybutyrolactone |
Non-Patent Citations (3)
Title |
---|
GAGE, DOUGLAS A. 等: "A new route for synthesis of dimethylsulfoniopropionate in marine algae", NATURE, vol. 387, pages 891 - 894 * |
SCIUTO, SEBASTIANO 等: "(-)-(S)-4-dimethylsulfonio-2-methoxybutyrate from the red alga Rytiphloea tinctoria", PHYTOCHEMISTRY, vol. 21, no. 1, pages 227 - 228 * |
SUMMERS, PETER S. 等: "Identification and stereospecificity of the first three enzymes of 3-dimethylsulfoniopropionate biosynthesis in a chlorophyte alga", PLANT PHYSIOLOGY, vol. 116, no. 1, pages 369 - 378 * |
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