CN101426921A - 用醇脱氢酶使光学活性仲醇外消旋化的方法 - Google Patents
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
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Abstract
通过采用至少一类E.C.1.1.1.醇脱氢酶诱导光学活性仲醇而使这些醇外消旋化的方法。
Description
本发明涉及一种酶催外消旋化光学活性仲醇的方法。
现有技术
仲醇脱氢酶催化仲醇氧化及对应酮还原成醇。
本发明涉及一种通过采用至少一种E.C.1.1.1.类醇脱氢酶诱导光学活性仲醇而使这些醇外消旋化的方法。
可用于本发明方法中的光学活性仲醇包括大量含有仲醇基团的结构不同的醇和化合物。
具有4-约20个碳原子链长的脂族醇适用,该脂族基团可能是支化的或未支化的,单-或多不饱和的或环状的或形成环状体系的一部分,所述环状体系例如为杂环体系如吗啉、吡咯、噻吩、吡唑、咪唑、噁唑、噻唑、吡啶、吡喃、嘧啶、哒嗪、吡嗪、苯并呋喃、吲哚及喹啉。
优选的脂族醇为2-丁醇、2-戊醇、2-己醇、3-己醇、2-庚醇、3-庚醇、2-辛醇、3-辛醇、2-壬醇及2-癸醇。
进一步适用的仲醇为具有芳基-烷基结构的那些,该芳族结构部分可能为同芳香性的或杂芳香性的。
优选的醇为具有任选取代的苯基、萘基或吡啶基作为芳族结构部分的那些。
特别优选的仲醇为任选取代的2-苯乙醇、2-苯丙醇、2-苯丁醇、2-苯戊醇及2-苯己醇。
这些醇也可被取代一次或多次,即一个或多个氢原子可被诸如F、Cl、Br、I、NH2、NHR、NR2、SH、CN、COOH、COOR、CO、CS、CNH、NO2的基团取代,其中R可为烷基或烷芳基。
适合作为醇脱氢酶的为E.C.1.1.1.酶分类的NAD-或NADP-依赖型氧化还原酶,特别是醇脱氢酶,优选依靠基因操作方法已从微生物中分离的或已分离的和/或改性的那些。改性可采用所谓的随机诱变方法或所谓的位点特异性诱变进行。
优选使用的醇脱氢酶为来自乳杆菌(Lactobacillus)属微生物,特别是克菲尔乳杆菌(Lactobacillus kefir)的那些以及来自红球菌(Rhodococcus)属微生物,特别是红平红球菌(Rhodococcus erythropolis)的那些。
这些醇脱氢酶可由商业获得(例如从Fluka)或可从向公众开放的菌株收藏库取得并采用已知方法分离。例如克菲尔乳杆菌DSM 20587,ATCC35411;红平红球菌DSM 43066,ATCC 25544。
在优选实施方案中,将多种不同的醇脱氢酶用作醇脱氢酶,优选普雷洛格(Prelog)特异性不同的那些,特别优选具有普雷洛格特异性的醇脱氢酶和具有反普雷洛格(anti-Prelog)特异性的第二醇脱氢酶。对于普雷洛格特异性的定义,参考文献Kurt Faber,Pure Appl.Chem.69,1613-1632,1997,特别是关于氧化还原反应的部分,该文献特意引入本文供参考。
热力学研究显示出采用任何醇脱氢酶都可能进行外消旋化。为了取得最大外消旋化率,外消旋化采用的醇脱氢酶应该对于氧化和还原具有最小对映/立体选择性。因为选择性尤其是温度的函数,所以采用在“正常”条件下具有选择性的酶(例如克菲尔乳杆菌醇脱氢酶)同样可能在高温进行外消旋化,如果其在这些条件下不会失去活性的话。具有高对映和立体选择性(E>200)的醇脱氢酶显示低的外消旋化活性。
在两种或多种酶体系中,醇脱氢酶体系的选择性由所用酶的选择性组成。当同时使用‘普雷洛格’酶(红平红球菌醇脱氢酶)和反‘普雷洛格’酶(菲尔乳杆菌醇脱氢酶)时,每一个都有与底物相关的高对映或立体选择性但是具有相反的立体优选性,体系的总选择性是1且外消旋化被加速。
按照本发明所采用的具有脱氢酶活性的酶在本发明方法中可用作游离或固定化酶。
本发明方法有利地在0-95℃,优选10-85℃,特别优选15-75℃的温度下进行。
本发明方法中的pH值有利地维持在4-12,优选4.5-9,特别优选5-8。
本发明方法可在额外溶剂中进行或在本身作为溶剂的底物中进行,视底物而定。适合的溶剂为所有允许酶催氧化还原反应的惯用有机溶剂,特别是醇类、酮类、醚类、烃类或这些物质的混合物。选择的溶剂有利地允许外消旋仲醇易于去除。
光学活性醇在本发明方法中是指显示出对映体富集的对映体。该方法优选使用的对映体纯度至少为70%ee,优选最小80%ee,特别优选最小90%ee,非常特别优选最小98%ee。
与起始醇(底物)相比,光学活性醇的外消旋化在这里意味着对映体纯度的减少,特别是对映体纯度减少了10%、20%、25%及30%。外消旋化不应理解为指对映体之比必须达到50:50,但该完全外消旋化代表了本发明的优选实施方案。
所用辅助因素(NAD/NADH或NADP/NADPH)的量对外消旋化并不重要,只要确保每摩尔酶存在至少1摩尔的NAD+或NADP,以确保酶-辅助因素复合体的完全形成。作为中间体形成的酮的浓度由所用NAD+/NADH比率和醇/酮氧化还原电势控制。
本发明方法也可有利地与辅助因素再生***结合。
本发明方法可连续和分批操作。
试验部分
所用醇(底物):
所用酶:
所用酶:
在2ml 容器中将50μl酶储液溶解于500μl磷酸盐缓冲溶液(50mM,pH7.5),并加入10μl的NAD+/NADH储液(50mg NADH/ml,30mgNAD+/ml)。通过加入2μl底物启动反应(48h,30℃/65℃,130rpm)。用500μl乙酸乙酯萃取使反应停止。
单酶体系
a:正负e.e.值与各(S)和(R)对映体的过量有关
b:反应48小时后的e.e.值
双酶体系
a:正负e.e.值与各(S)和(R)对映体的过量有关
b:反应48小时后的e.e.值
分析
气相色谱分析
气相色谱仪:Variant 3900气相色谱仪(FID)
柱:Chrompack Chirasil-DEX CB(25m×0.32mm×0.25μm,1.0巴H2)
a:℃/保留时间[min]/加热速率[℃/min]/℃/保留时间/加热速率/℃/保留时间[min]
b:正负e.e.值与各(S)和(R)对映体的过量有关
n.d.:不可测
醇的乙酰化(通常方法):
通过加入100μl乙酸酐/DMAP溶液并在30℃/130rpm条件下诱导60分钟进行衍生化。加入0.5ml水。取出有机相并用硫酸钠干燥。
Claims (6)
1.一种通过采用至少一种E.C.1.1.1.类醇脱氢酶诱导光学活性仲醇而使这些醇外消旋化的方法。
2.如权利要求1所述的方法,其中微生物醇脱氢酶用作醇脱氢酶。
3.如权利要求1所述的方法,其中来自乳杆菌(Lactobacillus)属或红球菌(Rhodococcus)属微生物的醇脱氢酶用作醇脱氢酶。
4.如权利要求1所述的方法,其中两种醇脱氢酶的混合物用作醇脱氢酶。
5.如权利要求4所述的方法,其中一种醇脱氢酶具有普雷洛格特异性,另一种醇脱氢酶具有反普雷洛格特异性。
6.如权利要求1所述的方法,其中所述诱导在不存在有机溶剂下或者在MTBE、甲苯、己烷或类似有机溶剂存在下进行。
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Application Number | Priority Date | Filing Date | Title |
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EP06112908 | 2006-04-21 | ||
EP06112908.6 | 2006-04-21 | ||
PCT/EP2007/053858 WO2007122182A1 (de) | 2006-04-21 | 2007-04-19 | Verfahren zur racemisierung optisch aktiver sekundärer alkohole unter verwendung von alkoholdehydrogenasen |
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CN101426921A true CN101426921A (zh) | 2009-05-06 |
CN101426921B CN101426921B (zh) | 2013-08-14 |
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CN200780013890.8A Expired - Fee Related CN101426921B (zh) | 2006-04-21 | 2007-04-19 | 用醇脱氢酶使光学活性仲醇外消旋化的方法 |
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US (1) | US7795004B2 (zh) |
EP (1) | EP2013352B1 (zh) |
JP (1) | JP5358428B2 (zh) |
CN (1) | CN101426921B (zh) |
AT (1) | ATE438729T1 (zh) |
DE (1) | DE502007001258D1 (zh) |
ES (1) | ES2328417T3 (zh) |
WO (1) | WO2007122182A1 (zh) |
Cited By (2)
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CN104313119A (zh) * | 2014-09-25 | 2015-01-28 | 常州大学 | 一种β-羟基羧酸酯羟基氧化酶的筛选方法 |
CN104313119B (zh) * | 2014-09-25 | 2017-01-04 | 常州大学 | 一种β-羟基羧酸酯羟基氧化酶的筛选方法 |
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DE4014573C1 (zh) * | 1990-05-07 | 1991-10-10 | Forschungszentrum Juelich Gmbh, 5170 Juelich, De | |
DE10218689A1 (de) * | 2002-04-26 | 2003-11-20 | Degussa | ADH aus Rhodococcus erythropolis |
KR20080072105A (ko) | 2004-08-26 | 2008-08-05 | 화이자 인코포레이티드 | 단백질 티로신 키나제 저해제 중간체의 제조를 위한거울상이성질선택적 생물학적 전환 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104313119A (zh) * | 2014-09-25 | 2015-01-28 | 常州大学 | 一种β-羟基羧酸酯羟基氧化酶的筛选方法 |
CN104313119B (zh) * | 2014-09-25 | 2017-01-04 | 常州大学 | 一种β-羟基羧酸酯羟基氧化酶的筛选方法 |
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WO2007122182A1 (de) | 2007-11-01 |
JP2009534023A (ja) | 2009-09-24 |
ES2328417T3 (es) | 2009-11-12 |
CN101426921B (zh) | 2013-08-14 |
EP2013352B1 (de) | 2009-08-05 |
US20090098623A1 (en) | 2009-04-16 |
EP2013352A1 (de) | 2009-01-14 |
US7795004B2 (en) | 2010-09-14 |
DE502007001258D1 (de) | 2009-09-17 |
JP5358428B2 (ja) | 2013-12-04 |
ATE438729T1 (de) | 2009-08-15 |
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