A new dehydrogenase from Clostridium acetobutylicum for asymmetric synthesis: dynamic reductive kinetic resolution entry into the Taxotere side chain

被引:42
作者
Applegate, Gregory A.
Cheloha, Ross W.
Nelson, David L.
Berkowitz, David B. [1 ]
机构
[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA
基金
美国国家科学基金会;
关键词
ENZYMATIC SCREENING ISES; BETA-AMINO ALCOHOLS; DIRECTED EVOLUTION; CHEMOENZYMATIC SYNTHESIS; SUBSTRATE-SPECIFICITY; EPOXIDE HYDROLASE; ALLYLIC AMINATION; BUILDING-BLOCKS; ATCC; 824; BUTANOL;
D O I
10.1039/c0cc04585c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An NADP-dependent alcohol dehydrogenase from Clostridium acetobutylicum (CaADH) has been expressed and characterized. CaADH enantioselectively reduces aromatic alpha-, beta- and gamma-keto esters to the corresponding D-hydroxy esters and provides a building block for the Taxotere side chain (95% yield, 95% de, 99% ee) by dynamic reductive kinetic resolution (DYRKR).
引用
收藏
页码:2420 / 2422
页数:3
相关论文
共 61 条
[1]   Expanding the Application Range of Aldolases: Novel Asymmetric Syntheses of α-Methylated β-Hydroxy α-Amino Acids and β-Amino Alcohols [J].
Baer, Katrin ;
Dueckers, Nina ;
Hummel, Werner ;
Groeger, Harald .
CHEMCATCHEM, 2010, 2 (08) :939-942
[2]   A template-based mnemonic for monoamine oxidase (MAO-N) catalyzed reactions and its application to the chemo-enzymatic deracemisation of the alkaloid (±)-crispine A [J].
Bailey, Kevin R. ;
Ellis, Andrew J. ;
Reiss, Renate ;
Snape, Timothy J. ;
Turner, Nicholas J. .
CHEMICAL COMMUNICATIONS, 2007, (35) :3640-3642
[3]   Reconstructing the clostridial n-butanol metabolic pathway in Lactobacillus brevis [J].
Berezina, Oksana V. ;
Zakharova, Natalia V. ;
Brandt, Agnieszka ;
Yarotsky, Sergey V. ;
Schwarz, Wolfgang H. ;
Zverlov, Vladimir V. .
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2010, 87 (02) :635-646
[4]   Isolation of a new butanol-producing Clostridium strain: High level of hemicellulosic activity and structure of solventogenesis genes of a new Clostridium saccharobutylicum isolate [J].
Berezina, Oksana V. ;
Brandt, Agnieszka ;
Yarotsky, Sergey ;
Schwarz, Wolfgang H. ;
Zverlov, Vladimir V. .
SYSTEMATIC AND APPLIED MICROBIOLOGY, 2009, 32 (07) :449-459
[5]   Chemoenzymatic and ring E-modular approach to the (-)-podophyllotoxin skeleton. Synthesis of 3',4',5'-tridemethoxy-(-)-podophyllotoxin [J].
Berkowitz, DB ;
Maeng, JH ;
Dantzig, AH ;
Shepard, RL ;
Norman, BH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9426-9427
[6]   In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination [J].
Berkowitz, DB ;
Shen, WJ ;
Maiti, G .
TETRAHEDRON-ASYMMETRY, 2004, 15 (18) :2845-2851
[7]  
Berkowitz DB, 2002, ANGEW CHEM INT EDIT, V41, P1603, DOI 10.1002/1521-3773(20020503)41:9<1603::AID-ANIE1603>3.0.CO
[8]  
2-D
[9]   ENANTIOMERICALLY ENRICHED ALPHA-VINYL AMINO-ACIDS VIA LIPASE-MEDIATED REVERSE TRANSESTERIFICATION [J].
BERKOWITZ, DB ;
PUMPHREY, JA ;
SHEN, QR .
TETRAHEDRON LETTERS, 1994, 35 (47) :8743-8746
[10]   Hydrolytic enzymatic transformation of advanced synthetic intermediates: on the choice of the organic cosolvent [J].
Berkowitz, DB ;
Hartung, RE ;
Choi, S .
TETRAHEDRON-ASYMMETRY, 1999, 10 (23) :4513-4520