Synthesis of γ-halogenated and long-chain β-hydroxy-α-amino acids and 2-amino-1,3-diols using threonine aldolases

被引：43

作者：

Steinreiber, Johannes ^{[1
]}

Fesko, Kateryna ^{[2
]}

Mayer, Clemens ^{[1
]}

Reisinger, Christoph ^{[1
]}

Schurmann, Martin ^{[3
]}

Griengl, Herfried ^{[1
,2
]}

机构：

[1] Res Ctr Appl Biocatalysis, A-8010 Graz, Austria

[2] Graz Univ Technol, Inst Organ Chem, A-8010 Graz, Austria

[3] DSM Pharmaceut Prod Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

来源：

TETRAHEDRON | 2007年 / 63卷 / 34期

基金：

奥地利科学基金会;

关键词：

enzymes; threonine aldolase; biocatalysis; amino acid; D-ERYTHRO-SPHINGOSINE; CERAMIDE GENERATION; ORGANIC-SYNTHESIS; GENE CLONING; NCIMB; 10558; L-SERINE; EFFICIENT; DIHYDROSPHINGOSINE; SPHINGANINES; DERIVATIVES;

D O I：

10.1016/j.tet.2007.06.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The L-and D-threonine aldolase catalyzed formation of gamma-halogenated and long-chain L-and D-3-alkylserine-derivatives 1-12, respectively, was shown starting from glycine and halogenated C-2-or C-4-C-12 aldehydes. LTA from Pseudomonas putida accepted all tested aldehydes with strongly varying diastereoselectivity (de up to 93%). Only aldehydes smaller than decanal were converted by DTA from Alcaligenes xylosoxidans with good selectivities (de up to 73%). Utilizing isobutanal enantio-and diastereopure D-syn-2-amino-3-hydroxy-4-methylpentanoic acid was obtained (ee> 99%, de> 95%), which was converted to the corresponding 2-amino-1,3-diol. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8088 / 8093

页数：6

共 50 条

[1] Novel threonine aldolases and their application to stereospecific synthesis of β-hydroxy-α-amino acids
Kataoka, M
Wada, M
Ikemi, M
Morikawa, T
Miyoshi, T
Shimizu, S
ENZYME ENGINEERING XIV, 1998, 864 : 318 - 322
[2] Synthesis of 2-amino-1,3-diols incorporating the cyclobutane ring
Perez-Fernandez, Marta
Avenoza, Alberto
Busto, Jesus H.
Peregrina, Jesus M.
Rodriguez, Fernando
TETRAHEDRON, 2008, 64 (38) : 9088 - 9092
[3] Complete stereodivergence in the synthesis of 2-amino-1,3-diols from allenes
Adams, Christopher S.
Grigg, R. David
Schomaker, Jennifer M.
CHEMICAL SCIENCE, 2014, 5 (08) : 3046 - 3056
[4] Threonine aldolases—screening, properties and applications in the synthesis of non-proteinogenic β-hydroxy-α-amino acids
Nina Dückers
Katrin Baer
Sabine Simon
Harald Gröger
Werner Hummel
Applied Microbiology and Biotechnology, 2010, 88 : 409 - 424
[5] Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols
Bajtel, Akos
Raji, Mounir
Haukka, Matti
Fulop, Ferenc
Szakonyi, Zsolt
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 983 - 990
[6] Asymmetric synthesis of 2-amino-1,3-diols and D-erythro-sphinganine
Enders, D
Müller-Hüwen, A
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (08) : 1732 - 1739
[7] Threonine aldolases-screening, properties and applications in the synthesis of non-proteinogenic β-hydroxy-α-amino acids
Dueckers, Nina
Baer, Katrin
Simon, Sabine
Groeger, Harald
Hummel, Werner
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2010, 88 (02) : 409 - 424
[8] α,α′-Dihydroxy Ketones and 2-Amino-1,3-diols: Synthetic and Process Strategies Using Biocatalysts
Hailes, H. C.
Dalby, P. A.
Lye, G. J.
Baganz, F.
Micheletti, M.
Szita, N.
Ward, J. M.
CURRENT ORGANIC CHEMISTRY, 2010, 14 (17) : 1883 - 1893
[9] An L-threonine aldolase for asymmetric synthesis of β-hydroxy-α-amino acids
Wang, Li-Chao
Xu, Lian
Xu, Xin-Qi
Su, Bing-Mei
Lin, Juan
CHEMICAL ENGINEERING SCIENCE, 2020, 226
[10] Characteristics of l-threonine transaldolase for asymmetric synthesis of β-hydroxy-α-amino acids
Xu, Lian
Wang, Li-Chao
Xu, Xin-Qi
Lin, Juan
CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (21) : 5943 - 5952

← 1 2 3 4 5 →