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

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