Protecting group free synthesis of urea-linked glycoconjugates: efficient synthesis of β-urea glycosides in aqueous solution

被引：6

作者：

Ichikawa, Yoshiyasu ^{[1
]}

Minami, Takahiro ^{[1
]}

Kusaba, Shohei ^{[1
]}

Saeki, Nobuyoshi ^{[1
]}

Tonegawa, Yuta ^{[1
]}

Tomita, Yumiko ^{[1
]}

Nakano, Keiji ^{[1
]}

Kotsuki, Hiyoshizo ^{[1
]}

Masuda, Toshiya ^{[2
]}

机构：

[1] Kochi Univ, Fac Sci, Kochi 7808520, Japan

[2] Univ Tokushima, Fac Integrated Arts & Sci, Tokushima 7708502, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 23期

关键词：

MODIFIED CURTIUS REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; GLUCOPYRANOSYL; CARBAMATE; CINODINE; WATER; GLYCOPEPTIDES; ANTIBIOTICS; REAGENTS;

D O I：

10.1039/c3ob42452a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the protecting group free synthesis of beta-urea-linked glycoconjugates has been developed. The one step process, involving reactions between urea and D-glucose, N-acetyl-D-glucosamine or D-xylose in acidic aqueous solution, furnishes the corresponding beta-urea glycosides in modest yields. This simple and efficient procedure is applicable to the synthesis of beta-urea tethered amino acid-carbohydrate conjugates.

引用

页码：3924 / 3931

页数：8

共 39 条

[1] GLYCOSYLUREAS .1. PREPARATION AND SOME REACTIONS OF D-GLUCOSYLUREAS AND D-RIBOSYLUREAS
BENN, MH
JONES, AS
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (OCT): : 3837 - 3841
[2] A facile stereoselective synthesis of α-glycosyl ureas
Bianchi, Aldo
Ferrario, Davide
Bernardi, Anna
[J]. CARBOHYDRATE RESEARCH, 2006, 341 (10) : 1438 - 1446
[3] Neoglycoconjugates, part 4.: New types of glycoconjugates:: O-glycosylated, N-glycosylated and O-,N-diglycosylated isoserine derivatives
Böttcher, C
Burger, K
[J]. TETRAHEDRON LETTERS, 2003, 44 (22) : 4223 - 4226
[4] Stereoselective synthesis of a C-glycosidic analog of N-glucoasparagine
Burkhart, F
Hoffmann, M
Kessler, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (11): : 1191 - 1192
[5] COUMAMIDINES, NEW BROAD-SPECTRUM ANTIBIOTICS OF THE CINODINE TYPE .2. ISOLATION AND STRUCTURAL ELUCIDATION
CHEN, RH
WHITTERN, DN
BUKO, AM
MCALPINE, JB
[J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (04) : 533 - 537
[6] Synthesis of S-linked glycosyl amino acids in aqueous solution with unprotected carbohydrates
Cohen, SB
Halcomb, RL
[J]. ORGANIC LETTERS, 2001, 3 (03) : 405 - 407
[7] Synthesis of glycoproteins
Davis, BG
[J]. CHEMICAL REVIEWS, 2002, 102 (02) : 579 - 601
[8] A NOVEL METHOD FOR THE SPECIFIC GLYCOSYLATION OF PROTEINS
DAVIS, NJ
FLITSCH, SL
[J]. TETRAHEDRON LETTERS, 1991, 32 (46) : 6793 - 6796
[9] GLYCOCINNASPERIMICIN-D, A NEW MEMBER OF GLYCOCINNAMOYLSPERMIDINE ANTIBIOTIC
DOBASHI, K
NAGAOKA, K
WATANABE, Y
NISHIDA, M
HAMADA, M
NAGANAWA, H
TAKITA, T
TAKEUCHI, T
UMEZAWA, H
[J]. JOURNAL OF ANTIBIOTICS, 1985, 38 (09) : 1166 - 1170
[10] Methods for anomeric carbon-linked and fused sugar amino acid synthesis: The gateway to artificial glycopeptides
Dondoni, A
Marra, A
[J]. CHEMICAL REVIEWS, 2000, 100 (12) : 4395 - +

← 1 2 3 4 →