One-Pot Transformation of Ketoximes into Optically Active Alcohols and Amines by Sequential Action of Laccases and Ketoreductases or ω-Transaminases

被引：15

作者：

Cordeiro, Raquel S. Correia ^{[1
,2
]}

Rios-Lombardia, Nicolas ^{[1
]}

Moris, Francisco ^{[1
]}

Kourist, Robert ^{[3
]}

Gonzalez-Sabin, Javier ^{[1
]}

机构：

[1] EntreChem SL, Vivero Ciencias Salud, Oviedo 33011, Spain

[2] Ruhr Univ Bochum, Jr Res Grp Microbial Biotechnol, Fac Biol & Biotechnol, D-44780 Bochum, Germany

[3] Graz Univ Technol, Petersgasse 14, A-8010 Graz, Austria

来源：

CHEMCATCHEM | 2019年 / 11卷 / 04期

基金：

欧盟地平线“2020”;

关键词：

one-pot reaction; oxime; alcohol dehydrogenase; transaminase; enzymatic cascade; SYNTHETIC APPLICATION; CASCADE CATALYSIS; DEHYDROGENASE; CAERULOMYCIN; BIOCATALYSIS; STEREOSELECTIVITY; ISOMERIZATION; PURIFICATION; COMBINATION; SYSTEMS;

D O I：

10.1002/cctc.201801900

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An enzymatic one-pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase-catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (omega-transaminase, omega-TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and overall conversions ranging from 83 to >99 % for alcohols and 70 to >99 % for amines. Likewise, the employment of exclusively 1 % (w/w) of Cremophor (R), a polyethoxylated castor oil, as co-solvent enabled to reach concentrations up to 100 mM in the chiral alcohols cascade.

引用

页码：1272 / 1277

页数：6

共 50 条

[21] ONE-POT TRANSFORMATION OF ALKYL BROMIDES INTO PRIMARY AMINES VIA THE STAUDINGER REACTION
KOZIARA, A
OSOWSKAPACEWICKA, K
ZAWADZKI, S
ZWIERZAK, A
SYNTHESIS-STUTTGART, 1985, (02): : 202 - 204
[22] One-pot two-stage biocatalytic upgrading of biomass-derived aldehydes to optically active β-amino alcohols via sequential hydroxymethylation and asymmetric reduction amination
Suo, Yin-Hua
Zhang, Jing-Qi
Qi, Ning
Huang, Shuang-Ping
Gao, Hang
Gao, Li-Li
Zhang, Chao-Feng
He, Yu-Cai
Zhang, Jian-Dong
GREEN CHEMISTRY, 2024, 26 (02) : 927 - 935
[23] One-pot acylation and fractional crystallization: preparation of optically active serinol monobenzoates
Sugiyama, S
Inoue, T
Ishii, K
TETRAHEDRON-ASYMMETRY, 2003, 14 (15) : 2153 - 2160
[24] One-Pot Synthesis of Imines and Secondary Amines by Pd-Catalyzed Coupling of Benzyl Alcohols and Primary Amines
Kwon, Min Serk
Kim, Sungjin
Park, Sungho
Bosco, William
Chidrala, Ravi Kumar
Park, Jaiwook
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (07): : 2877 - 2879
[25] Efficient Synthesis of Phosphonamidates through One-Pot Sequential Reactions of Phosphonites with Iodine and Amines
Chen, Xunwei
Luo, Wenjun
Wang, Yanlin
Li, Zikang
Ma, Xiaorui
Peng, Ai-Yun
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (63) : 14474 - 14480
[26] One-Pot Sequential Catalytic Hydration of Alkynes and α-Alkylation with Alcohols for the Synthesis of α-Alkylated Ketones
Ma, Juan
Wang, Nana
Li, Feng
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (09) : 940 - 947
[27] One-pot enantioselective synthesis of optically active homoallylic alcohols from allyl halides (vol 48, pg 306, 2000)
Nakajima, M
Saito, M
Hashimoto, S
CHEMICAL & PHARMACEUTICAL BULLETIN, 2000, 48 (06) : 895 - 895
[28] One-pot transformation of p-toluenesulfonates of 2,3-epoxy alcohols into allylic alcohols
Habashita, H
Kawasaki, T
Akaji, M
Tamamura, H
Kimachi, T
Fujii, N
Ibuka, T
TETRAHEDRON LETTERS, 1997, 38 (48) : 8307 - 8310
[29] One-Pot Synthesis of α,β-Unsaturated γ-Lactones and Lactams via a Sequential trans-Hydroalumination and Catalytic Carboxylation of Propargyl Alcohols and Amines with Carbon Dioxide
Yoo, Woo-Jin
Chen, Wenlong
Nguyen, Thanh V. Q.
Kobayashi, Shu
ORGANIC LETTERS, 2020, 22 (06) : 2328 - 2332
[30] Organocatalysis in Natural Product Synthesis: A Simple One-Pot Approach to Optically Active β-Diols
Andersen, Nikolaj Rojkjaer
Hansen, Signe Grann
Bertelsen, Soren
Jorgensen, Karl Anker
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3193 - 3198

← 1 2 3 4 5 →