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

[21] New approach to the synthesis of β-hydroxy-α-amino acids using (arylthio)nitrooxiranes
Jackson, Richard F.W.
Palmer, Nicholas J.
Wythes, Martin J.
Clegg, William
Elsegood, Mark R.J.
Journal of Organic Chemistry, 1995, 60 (20):
[22] Synthesis of 1,3-Amino Alcohols, 1,3-Diols, Amines, and Carboxylic Acids from Terminal Alkynes
Zeng, Mingshuo
Herzon, Seth B.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8604 - 8618
[23] Synergistic Photoenzymatic Catalysis Enables Synthesis of a-Tertiary Amino Acids Using Threonine Aldolases
Ouyang, Yao
Page, Claire G.
Bilodeau, Catherine
Hyster, Todd K.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (20) : 13754 - 13759
[24] Efficient enantioselective synthesis of α-hydroxy-β-amino acids using the claisen and curtius rearrangements
Jung, DY
Kang, S
Chang, S
Kim, YH
SYNLETT, 2006, (01) : 86 - 90
[25] A Useful Allene for the Stereoselective Synthesis of Protected Quaternary 2-Amino-2-vinyl-1,3-diols
Rodriguez, Aleix
Ariza, Xavier
Contreras, Mitguel A.
Garcia, Jordi
Lloyd-Williams, Paul
Mercadal, Nerea
Sanchez, Carolina
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03): : 1851 - 1855
[26] 2-Amino-1,3-propane diols: a versatile platform for the synthesis of aliphatic cyclic carbonate monomers
Venkataraman, Shrinivas
Veronica, Natalia
Voo, Zhi Xiang
Hedrick, James L.
Yang, Yi Yan
POLYMER CHEMISTRY, 2013, 4 (10) : 2945 - 2948
[27] Enzymatic synthesis of beta-hydroxy-alpha-amino acids based on recombinant D- and L-threonine aldolases
Kimura, T
Vassilev, VP
Shen, GJ
Wong, CH
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) : 11734 - 11742
[28] A SIMPLE METHOD FOR THE SYNTHESIS OF LONG-CHAIN ALKYL ESTERS OF AMINO-ACIDS
PENNEY, CL
SHAH, P
LANDI, S
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09): : 1457 - 1459
[29] STUDIES IN SYNTHESIS OF LONG-CHAIN HYDROXY-ACIDS .2.
MALANI, C
MINNIKIN, DE
POLGAR, N
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (OCT): : 5562 - +
[30] PHOSGENE AS A REAGENT FOR THE ENANTIOMERIC RESOLUTION OF 1,2-DIOLS,ALPHA-AMINO AND 1,3-DIOLS, ALPHA-AMINO ALCOHOLS, ALPHA-HYDROXY ACIDS, AND N-METHYL-ALPHA-AMINO ACIDS BY GAS-CHROMATOGRAPHY
KONIG, WA
STEINBACH, E
ERNST, K
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1984, 23 (07) : 527 - 528

← 1 2 3 4 5 →