JP2019526643A - 1,3−脂肪ジオール化合物およびそれらの誘導体 - Google Patents
1,3−脂肪ジオール化合物およびそれらの誘導体 Download PDFInfo
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- JP2019526643A JP2019526643A JP2019535222A JP2019535222A JP2019526643A JP 2019526643 A JP2019526643 A JP 2019526643A JP 2019535222 A JP2019535222 A JP 2019535222A JP 2019535222 A JP2019535222 A JP 2019535222A JP 2019526643 A JP2019526643 A JP 2019526643A
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- Prior art keywords
- diol
- fatty
- dodecene
- exemplary embodiment
- carbon
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Abstract
Description
本開示は概して、例えば、洗剤および界面活性剤の生産における工業用物質およびプロセスの構成成分として、化粧品中および食品中の乳化剤、軟化剤、および増粘剤として、工業用溶媒および可塑剤などとしての使用に好適なスペシャリティケミカルの分野に関する。
本出願は、2016年9月14日出願の米国仮出願第62/394,537号の利益を主張し、この特許の全体が、参照により本明細書に組み込まれる。
脂肪アルコール、特に脂肪ジオール(または脂肪族ジオール)は、商業的および工業的用途を有する両親媒性分子である。例えば、脂肪アルコールは、化粧品中および食品中の軟化剤および増粘剤として、ならびに工業用溶媒、可塑剤、潤滑剤、乳化剤、ポリマーの構成単位などとして用途を見出す(例えば、H.Maag(1984)Journal of the American Oil Chemists’ Society61(2):259−267(非特許文献1)を参照されたい)。特に有用なのは、1,3−脂肪ジオールである。
本開示の一態様は、単一のΔ5二重結合を有し、炭素番号1(C−1)でヒドロキシ基を有し、炭素番号3(C−3)でヒドロキシ基を有する、炭素12個の非分枝状不飽和脂肪ジオールであって、キラル中心が、C−3に存在し、脂肪ジオールが、式IIの一般化学式を有する、脂肪ジオールを提供する。
式中、nは、0、1、2、3、4、5、6、7、8、9、10、11、12、13、および14から選択される整数であり、R1およびR2は各々独立して、H、単糖類のアノマー炭素において結合した単糖類、二糖類のアノマー炭素において結合した二糖類、アノマー炭素において結合した三糖類、およびアノマー炭素において結合した多糖類からなる群から選択される。一例示的な実施形態において、R1およびR2の両方がHというわけではない。別の例示的な実施形態において、R1もR2もHではない。別の例示的な実施形態において、単糖類は、ペントース糖およびヘキソース糖から選択される。別の例示的な実施形態において、ヘキソース糖は、アロース、アルトロース、グルコース、マンノース、グロース、イオドース、ガラクトース、またはタロースから選択される。別の例示的な実施形態において、二糖類、三糖類、および多糖類は、ペントース糖、ヘキソース糖、またはそれらのいずれか2つ以上の混合物から選択される糖を含む。別の例示的な実施形態において、ヘキソース糖は、アロース、アルトロース、グルコース、マンノース、グロース、イオドース、ガラクトース、タロース、またはそれらのいずれか2つ以上の混合物から選択される。別の例示的な実施形態において、R1およびR2は、異なる単糖類である。別の例示的な実施形態において、R1およびR2は、同じ単糖類である。別の例示的な実施形態において、単糖類、二糖類、三糖類、および多糖類は、アロース、アルトロース、グルコース、マンノース、グロース、イオドース、ガラクトース、タロース、またはそれらのいずれか2つ以上の混合物から選択されるヘキソース糖を含む。別の例示的な実施形態において、単糖類、二糖類、三糖類、および多糖類は、フラノース糖、ピラノース糖、またはそれらのいずれか2つ以上の混合物から選択される糖を含む。
式中、mは、1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、および18から選択される整数であり、R3およびR4は各々独立して、H、単糖類のアノマー炭素において結合した単糖類、二糖類のアノマー炭素において結合した二糖類、アノマー炭素において結合した三糖類、およびアノマー炭素において結合した多糖類からなる群から選択される。一例示的な実施形態において、R3およびR4の両方がHというわけではない。別の例示的な実施形態において、R3もR4もHではない。別の例示的な実施形態において、単糖類は、ペントース糖およびヘキソース糖から選択される。別の例示的な実施形態において、ヘキソース糖は、アロース、アルトロース、グルコース、マンノース、グロース、イオドース、ガラクトース、またはタロースから選択される。別の例示的な実施形態において、二糖類、三糖類、および多糖類は、ペントース糖、ヘキソース糖、またはそれらのいずれか2つ以上の混合物から選択される糖を含む。別の例示的な実施形態において、ヘキソース糖は、アロース、アルトロース、グルコース、マンノース、グロース、イオドース、ガラクトース、タロース、またはそれらのいずれか2つ以上の混合物から選択される。別の例示的な実施形態において、R3およびR4は、異なる単糖類である。別の例示的な実施形態において、R3およびR4は、同じ単糖類である。別の例示的な実施形態において、単糖類、二糖類、三糖類、および多糖類は、アロース、アルトロース、グルコース、マンノース、グロース、イオドース、ガラクトース、タロース、またはそれらのいずれか2つ以上の混合物から選択されるヘキソース糖を含む。別の例示的な実施形態において、単糖類、二糖類、三糖類、および多糖類は、フラノース糖、ピラノース糖、またはそれらのいずれか2つ以上の混合物から選択される糖を含む。
定義
本明細書および添付の特許請求の範囲で使用される場合、要素を記載する文脈における「1つの(a)」および「1つの(an)」および「その(the)」などの単数形冠詞ならびに類似の参照対照は、別段本明細書で示されない限り、または文脈が明らかに矛盾しない限り、単数形および複数形の両方を包含するように解釈されるべきである。
A.一般的な方法
本開示は、組み換え遺伝学における慣例的な技術を利用する。分子生物学および遺伝学における一般的な方法および用語を開示する基本的なテキストとしては、例えば、Sambrook et al.,Molecular Cloning,a Laboratory Manual,Cold Spring Harbor Press4th edition(Cold Spring Harbor,N.Y.2012)、Current Protocols in Molecular Biology Volumes1−3,John Wiley&Sons,Inc.(1994−1998)が挙げられる。本開示また、生化学の分野における慣例的な技術も利用する。生化学における一般的な方法および用語を開示する基本的なテキストとしては、例えば、Lehninger Principles of Biochemistry sixth edition,David L.Nelson and Michael M.Cox eds.W.H.Freeman(2012)が挙げられる。本開示は、工業発酵における慣例的な技術も利用する。発酵における一般的な方法および用語を開示する基本的なテキストとしては、例えば、Principles of Fermentation Technology,3rd Edition by Peter F.Stanbury,Allan Whitaker and StephenJ.Hall.Butterworth−Heinemann(2016)、Fermentation Microbiology and Biotechnology,2nd Edition,E.M.T.El−Mansi,C.F.A.Bryce,Arnold L.Demain and A.R.Allman eds.CRC Press(2007)が挙げられる。本開示は、有機化学の分野における慣例的な技術も利用する。有機化学における一般的な方法および用語を開示する基本的なテキストとしては、例えば、Practical Synthetic Organic Chemistry:Reactions,Principles,and Techniques,Stephane Caron ed.,John Wiley and Sons Inc.(2011)、The Synthetic Organic Chemist’s Companion,Michael C.Pirrung,John Wiley and Sons Inc.(2007)、Organic Chemistry,9th Edition−Francis Carey and Robert Giuliano,McGraw Hill(2013)が挙げられる。
上記に考察されるように、1,3−脂肪ジオールは、特に有用な分子である。誘導体を形成する反応のために2つのヒドロキシル官能基を提供することに加えて、1,3−脂肪ジオールの3−ヒドロキシ部分は、第3の炭素(C−3)でキラル中心を形成し、これにより、1,3−脂肪ジオールは、医薬品、栄養補助食品、殺虫剤、除草剤、香料、芳香剤、溶媒、生物活性化合物などのキラル的に重要な化合物の生成用のシントンとして有用となる。
本明細書に開示される1,3−脂肪ジオールの全ては、2つのアルコール基を含み、かつC−3炭素にキラル中心を含む。加えて、本明細書に開示される不飽和1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールはまた、二重結合も含む。したがって、本明細書に開示される1,3−脂肪ジオールは、多様な化学反応を受けて、多種多様な分子を形成することができる。したがって、本明細書に開示される1,3−脂肪ジオールのいずれか自体の(例えば、界面活性剤としての)価値に加えて。例示的な実施形態において、本明細書に開示される1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールは、無限の数の特有かつ有用な分子の構成単位として機能する。
本明細書に開示される不飽和1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールは、二重結合を含む。1,3−脂肪ジオールが生成および/または加工される方法(本明細書の下記を参照されたい)に応じて、二重結合は、(Z)または(E)のいずれであってもよい。したがって、本明細書に開示される不飽和1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールは、例えば、重合、アルキル化、メタセシスなどを含む、二重結合に関連する化学反応に関与することができる。炭素−炭素二重結合を利用する化学反応は、当該技術分野において既知である(例えば、Practical Synthetic Organic Chemistry:Reactions,Principles,and Techniques,Stephane Caron ed.(上記)を参照されたい)。
本明細書に開示される1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオール、9−ヘキサデセン−1,3−ジオールなどの全ては、化学反応に利用可能である2つのヒドロキシル官能基を含む。
C−3炭素にキラル中心を有する、例えば、1,3−脂肪ジオール(例えば、5−ドデセン−1,3−ジオール)などのキラル分子は、立体化学によって影響を受ける化合物(例えば、医薬品、栄養補助食品など)の合成のための構成単位である。キラル薬物のほとんどの異性体は、例えば、薬理、毒性、薬物動態、生体認識、代謝などの生物学的活性の顕著な差を呈するため、キラリティーは、例えば、薬物設計において考慮すべき重要な特性である。実際に、適切な鏡像異性体の選択は、分子の生物学的特性に対して重大な影響を有し得る。
いくつかの例示的な実施形態において、本明細書に開示される1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオール、9−ヘキサデセン−1,3−ジオールなどのヒドロキシル官能基を使用して、非イオン性界面活性剤が調製される。
例示的な実施形態において、本明細書に開示される1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールのヒドロキシル部分は、アルキルポリグリコシドを提供する糖との反応に利用可能である。アルキルポリグリコシドは、糖および脂肪アルコール由来の非イオン性界面活性剤のクラスであり、当該技術分野において周知である(例えば、Alkyl Polyglycosides:Technology,Properties,Applications,Karlheinz Hill;Wolfgang von Rybinski;Gerhard Stoll,eds.Wiley(2008)、Novel Surfactants:Preparation Applications And Biodegradability,Surfactant Science Series.Volume114Second Edition,Krister Holmberg ed.Marcel Dekker:New York and Basel,Switzerland.2003を参照されたい)。したがって、例示的な実施形態において、本明細書に開示される1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールを、例えば、キシロース、ガラクトース、マンノース、グルコースなどと反応させて、新しく有用な特性を有するアルキルポリグリコシドを形成する。
であり得、R5は独立して出現毎に、Hまたは
であり、rは、1、2、3、4、5、6、7、8、9、または10の整数であり、sは、1、2、3、4、5、6、7、8、9、または10である。本明細書の任意の実施形態において、R1、R2、R3、R4、およびR5は各々独立して、アロース、アルトロース、グルコース、マンノース、グロース、イオドース、ガラクトース、タロース、あるいは(R1、R2、R3、R4、およびR5のいずれか2つ以上が異なる単糖類である場合、ならびに/または任意の1つ以上の二糖類、三糖類、もしくは多糖類の場合)それらのいずれか2つ以上の混合物を含み得る。本明細書の任意の実施形態において、上記に示されるように、R1、R2、R3、R4、および/またはR5が単糖類、二糖類、三糖類、および/または多糖類である場合、R1、R2、R3、R4、および/またはR5は、α−グリコシド結合またはβ−グリコシド結合を介して結合し得る。更に、上記の構造式に示される、R1、R2、R3、R4、および/またはR5の二糖類、三糖類、および/または多糖類は、α−グリコシド結合、β−グリコシド結合、または(三糖類および/もしくは多糖類の場合)それらのいずれか2つ以上の混合物を含む糖類であり得る。
アルキルポリグリコシドは、多数の工業用物質および目的に有利に組み込むことができる特に有用な分子である。実際に、アルキルポリグリコシドは、例えば、化粧品中および食品中の乳化剤、軟化剤、および増粘剤として、農業配合物中、例えば、標的(例えば、葉のワックス状表面)へ活性成分を送達するための殺虫剤配合物中で、工業用溶媒として、石油の回収を増強するために石油およびガス産業において、可塑剤として、界面活性剤および洗剤として、ならびに界面活性剤および洗剤の生産などにおいて用途を見出す。
例示的な実施形態において、5−ドデセン−1,3−ジオールのヒドロキシル部分は、新規のアルコールエトキシレート、エトキシサルフェート、プロポキシレートおよびブトキシレート、脂肪アルコールポリグリコールエーテルなどを調製するためのエトキシ化に利用可能である。アルコールエトキシレートは、当該技術分野において既知である(例えば、米国特許第4,223,163号、Surfactants.In Elvers,Barbara, et al.Ullmann’s Encyclopedia of Industrial Chemistry.Weinheim,GER:Wiley−VCHを参照されたい)。
いくつかの例示的な実施形態において、5−ドデセン−1,3−ジオールのヒドロキシル官能基を使用して、ポリウレタンが調製される。
上記に明記されるように、1,3−ジオール構造は、例えば、類似した鎖長の1,2−ジオールよりも立体障害が少なく、ポリマー形成を補助する。
a.生物学的合成の一般経路
5−ドデセン−1,3−ジオールは、当該技術分野において既知である任意の方法によって作製することができる。上記に考察されるように、不飽和脂肪アルコールは、石油からの生成が困難である。むしろ、不飽和脂肪アルコールは、典型的には植物起源および動物起源の脂肪および油などの非石油供給源の加工から生成される(例えば、E.F.Hill,et al.(1954)Ind.Eng.Chem.,46(9):1917−1921を参照されたい)。そのようなプロセスは厄介であり、汚染を引き起こす可能性があり、典型的には限られた種類の不飽和脂肪アルコール生成物しか生成しない。
本明細書に開示される1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールの3−ヒドロキシ官能性は、C−3で立体中心を形成し、分子のキラリティー点を提供する。上記に明記されるように、キラリティーは、例えば、ポリマー性能、生物活性、薬学的効力などを含む、分子用途を定義する上での有用な分子特質であり得る。
本明細書で使用される場合、発酵は、組み換え宿主細胞により有機材料を標的物質に変換することを広く指す。例えば、これは、炭素供給源を含む培地中で組み換え宿主細胞の培養物を増殖させることによって、組み換え宿主細胞により炭素供給源を脂肪酸誘導体(1,3−脂肪ジオールなど)に変換することを含む。1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールなどの標的物質の生成を許容する条件は、宿主細胞が所望の生成物(1,3−脂肪ジオール組成物など)を生成することを可能にする任意の条件である。好適な条件には、例えば、典型的な発酵条件が含まれ、例えば、Principles of Fermentation Technology,3rd Edition(2016)(上記)、Fermentation Microbiology and Biotechnology,2nd Edition(2007)(上記)を参照されたい。
上記に考察されるように、1,3−脂肪ジオールを生成するように操作された組み換え宿主細胞によって生成される不飽和1,3−脂肪ジオール、例えば、5−ドデセン−1,3−ジオールの二重結合は、主に(Z)配置である。
バイオ生成物、例えば、節IIa〜IId.で上記に考察される操作された微生物を利用して生成される5−ドデセン−1,3−ジオールを含む組成物は、再生可能な供給原から(例えば、再生可能な供給原料由来の単純な炭素供給源から)生成され、したがって、新たな物質の組成物である。これらの新たなバイオ生成物は、二重炭素同位体フィンガープリント法または14C年代測定に基づいて、石油化学由来炭素の有機化合物から区別することができる。加えて、生物由来炭素の特定の供給源(例えば、グルコース対グリセロール)は、当該技術分野において既知である方法によって、二重炭素同位体フィンガープリント法により決定することができる(例えば、米国特許第7,169,588号、WO2016/011430A1などを参照されたい)。
以下の実施例は、発酵による5−ドデセン−1,3−ジオールの生成を例示する。脂肪アルコールおよび1,3ジオールの生成のために操作された大腸菌株を使用する発酵によって、5−ドデセン−1,3−ジオールを生成した。その後、結果として得られた発酵ブロスからこれらの1,3−脂肪ジオールを精製した。
以下の実施例は、遠心分離した発酵ブロスからの1,3ジオールの精製を例示する。
以下の実施例は、ガスクロマトグラフィー(GC)および質量分析法(MS)を使用して脂肪アルコールおよび1,3ジオールを分析評価するための一例示的な方法を例示する。
以下の実施例は、本明細書の下記で実施例5に開示される化学合成経路を介した5−ドデセン−1,3−ジオールの調製に有用な(S)−2−[2−(ベンジルオキシ)エチル]オキシランの合成を例示する。これは、予測に基づく一実施例である。
以下の実施例は、合成化学アプローチを使用して、(R,Z)−ドデカ−5−エン−1,3−ジオール(すなわち、(R,Z)−5−ドデセン−1,3−ジオール)を生成するための方法を例示する。これは、予測に基づく一実施例である。
以下の実施例は、(R)−ドデカン−1,3−ジオールの化学合成を例示する。これは、予測に基づく一実施例である。
以下の実施例は、グリコシル化(R,Z)−ドデカ−5−エン−1,3−ジオールの一例示的な2ステップ合成を例示する。これは、予測に基づく一実施例である。
以下の実施例は、(R,Z)−ドデカ−5−エン−1,3−ジオールの調製のための一例示的な1ステップ方法を例示する。これは、予測に基づく一実施例である。
logP=log([化合物]n−オクタノール/([化合物]水) 等式1
Claims (12)
- 前記二重結合が、(Z)配置である、請求項1に記載の脂肪ジオール。
- 前記二重結合が、(E)配置である、請求項1に記載の脂肪ジオール。
- C−3の前記キラル中心が、R配置を有する、請求項1に記載の脂肪ジオール。
- C−3の前記キラル中心が、S配置を有する、請求項1に記載の脂肪ジオール。
- 前記二重結合が、(Z)配置であり、C−3の前記キラル中心が、R配置を有する、請求項1に記載の脂肪ジオール。
- 前記二重結合が、(Z)配置である、請求項7に記載の脂肪ジオール。
- 前記二重結合が、(E)配置である、請求項7に記載の脂肪ジオール。
- C−3の前記キラル中心が、R配置を有する、請求項7に記載の脂肪ジオール。
- C−3の前記キラル中心が、S配置を有する、請求項7に記載の脂肪ジオール。
- 前記二重結合が、(Z)配置であり、C−3の前記キラル中心が、R配置を有する、請求項7に記載の脂肪ジオール。
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