Rabbit muscle aldolase (RAMA) as a catalyst in a new approach for the synthesis of 3-deoxy-D-manno-2-octulosonic acid and analogues

被引:14
作者
Crestia, D [1 ]
Guérard, C [1 ]
Bolte, J [1 ]
Demuynck, C [1 ]
机构
[1] Univ Blaise Pascal, Lab Chim Org Biol, UMR CNRS 6504, F-63177 Clermont Ferrand, France
关键词
carbon-carbon bond formation; aldolase; KDO; KDO analogues;
D O I
10.1016/S1381-1177(00)00074-6
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A new approach leading to 3-deoxy-D-manno-2-octulosonic acid (KDO) and 4-deoxy-KDO is described. The key step is the formation of the C-5-C-6 bond catalysed by fructose-1,6-bisphosphate aldolase, which controls the stereochemistry of these two centres. The important step of the aldehyde substrates (la, Ib, Ic) synthesis is the Barbier reaction of ethyl-bromomethylacrylate or bromomethylacrylonitrile with the monoacetal of glyoxal in the presence of indium. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:207 / 212
页数:6
相关论文
共 29 条
[1]  
ANDERSON FM, 1983, ACS S SERIES, V231
[2]   Fructose-1,6-bisphosphate aldolase and transketolase: Complementary tools for the de novo syntheses of monosaccharides and analogues [J].
Andre, C ;
Demuynck, C ;
Gefflaut, T ;
Guerard, C ;
Hecquet, L ;
Lemaire, M ;
Bolte, J .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1998, 5 (1-4) :113-118
[3]   THE USE OF ASPERGILLUS-TERREUS EXTRACTS IN THE PREPARATIVE SYNTHESIS OF 2-KETO-3-DEOXY-ULOSONIC ACIDS [J].
AUGE, C ;
DELEST, V .
TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :863-866
[4]   The invention of radical reactions .36. Synthetic studies related to 3-deoxy-D-manno-2-octulosonic acid (KDO) [J].
Barton, DHR ;
Jaszberenyi, JC ;
Liu, WS ;
Shinada, T .
TETRAHEDRON, 1996, 52 (08) :2717-2726
[5]   SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONATE-8-PHOSPHATE (KDO-8-P) FROM D-ARABINOSE - GENERATION OF D-ARABINOSE-5-PHOSPHATE USING HEXOKINASE [J].
BEDNARSKI, MD ;
CRANS, DC ;
DICOSIMO, R ;
SIMON, ES ;
STEIN, PD ;
WHITESIDES, GM .
TETRAHEDRON LETTERS, 1988, 29 (04) :427-430
[6]   SYNTHESIS OF ALDOSE SUGARS FROM HALF-PROTECTED DIALDEHYDES USING RABBIT MUSCLE ALDOLASE [J].
BORYSENKO, CW ;
SPALTENSTEIN, A ;
STRAUB, JA ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9275-9276
[7]   Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-β-KDO [J].
Burke, SD ;
Sametz, GM .
ORGANIC LETTERS, 1999, 1 (01) :71-74
[8]   IMPROVED SYNTHESES OF ETHYL ALPHA-(BROMOMETHYL)ACRYLATE AND 2-METHYLENE-1,3-PROPANEDIOL VIA ETHYL ALPHA-(HYDROXYMETHYL)ACRYLATE [J].
BYUN, HS ;
REDDY, KC ;
BITTMAN, R .
TETRAHEDRON LETTERS, 1994, 35 (09) :1371-1374
[9]   A NEW SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) [J].
COUTROT, P ;
GRISON, C ;
TABYAOUI, M .
TETRAHEDRON LETTERS, 1993, 34 (32) :5089-5092
[10]   Chain extension of aldonolactones by samarium iodide mediated Dreiding-Schmidt reactions and samarium assisted Imamoto reactions [J].
Csuk, R ;
Horing, U ;
Schaade, M .
TETRAHEDRON, 1996, 52 (29) :9759-9776