Synthesis of β-D-Galp-(1→4)-α-D-Manp methanephosphonate, a substrate analogue for the elongating α-D-mannosyl phosphate transferase in the Leishmania

被引：15

作者：

Borodkin, VS ^{[1
]}

Ferguson, MAJ ^{[1
]}

Nikolaev, AV ^{[1
]}

机构：

[1] Univ Dundee, Sch Life Sci, Div Biol Chem & Mol Microbiol, Dundee DD1 4HN, Scotland

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 31期

基金：

英国惠康基金;

关键词：

carbohydrates; phosphonic acids and derivatives;

D O I：

10.1016/S0040-4039(01)00961-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5305 / 5308

页数：4

共 21 条

[1] THE SYNTHESIS OF ISOPRENOID (PHOSPHINYLMETHYL)PHOSPHONATES
BILLER, SA
FORSTER, C
[J]. TETRAHEDRON, 1990, 46 (19) : 6645 - 6658
[2] VINYLATION ELECTROPHILIC CYCLIZATION OF ALDOPENTOSES - EASY AND STEREOSELECTIVE ACCESS TO C-GLYCOPYRANOSIDES OF RARE SUGARS
BOSCHETTI, A
NICOTRA, F
PANZA, L
RUSSO, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) : 4181 - 4185
[3] Stereoselective synthesis of the isosteric phosphono analogues of N-acetyl-alpha-D-glucosamine 1-phosphate and N-acetyl-alpha-D-mannosamine 1-phosphate
Casero, F
Cipolla, L
Lay, L
Nicotra, F
Panza, L
Russo, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) : 3428 - 3432
[4] SYNTHESIS OF PHOSPHONATE ANALOGS OF ALPHA-D-GLUCOPYRANOSYL AND ALPHA-D-GALACTOPYRANOSYL PHOSPHATE
CHMIELEWSKI, M
BEMILLER, JN
CERRETTI, DP
[J]. CARBOHYDRATE RESEARCH, 1981, 97 (02) : C1 - C4
[5] Direct synthesis of the isosteric phosphono analogues of α-L-rhamnose 1-phosphate and β-L-fucose 1-phosphate
Cipolla, L
La Ferla, B
Panza, L
Francesco, N
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1998, 17 (07) : 1003 - 1013
[6] SELECTIVE ACETOLYSIS OF PRIMARY BENZYL ETHERS
EBY, R
SONDHEIMER, SJ
SCHUERCH, C
[J]. CARBOHYDRATE RESEARCH, 1979, 73 (AUG) : 273 - 276
[7] PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES
ENGEL, R
[J]. CHEMICAL REVIEWS, 1977, 77 (03) : 349 - 367
[8] FRISCHE K, 1994, LIEBIGS ANN CHEM, P297
[9] Parasite glycoconjugates.: Part 9.: Synthesis of dec-9-enyl β-D-galactopyranosyl-(1→4)-α-D-mannopyranosyl phosphate and its epimers at the D-galactose moiety, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania
Ivanova, IA
Ross, AJ
Ferguson, MAJ
Nikolaev, AV
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12): : 1743 - 1753
[10] SYNTHESIS OF C-ARABINOFURANOSYL COMPOUNDS - PHOSPHONATE AND CARBOXYLATE ISOSTERES OF D-ARABINOSE 1,5-BISPHOSPHATE
MARYANOFF, BE
NORTEY, SO
INNERS, RR
CAMPBELL, SA
REITZ, AB
LIOTTA, D
[J]. CARBOHYDRATE RESEARCH, 1987, 171 : 259 - 278

← 1 2 3 →