Reactivity of melezitose and raffinose under Mitsunobu reaction conditions

被引：15

作者：

Besset, Celine ^{[1
,2
]}

Chambert, Stephane ^{[1
,2
]}

Queneau, Yves ^{[1
,2
]}

Kerverdo, Sebastien ^{[3
]}

Rolland, Herve ^{[3
]}

Guilbot, Jerome ^{[3
]}

机构：

[1] Inst Natl Sci Appl, Inst Chim & Biochim Mol & Supramol, Chim Organ Lab, F-69621 Villeurbanne, France

[2] Univ Lyon 1, Univ Lyon, ICBMS, CNRS,UMR 5246,INSA Lyon,CPE Lyon, F-69622 Villeurbanne, France

[3] SEPPIC, F-81105 Castres, France

来源：

CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 05期

关键词：

sugar esters; raffinose; melezitose; Mitsunobu reaction; anhydro sugars;

D O I：

10.1016/j.carres.2008.01.041

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：

The reactivity of melezitose and raffinose under Mitsunobu conditions was studied within the scope of the use of trisaccharides for the synthesis of fatty acid esters. Melezitose led to esters with preferential substitution at primary positions following the order of reactivity 6 '' > 6 > 6'. Raffinose proved to be very reluctant toward ester formation in these conditions, leading mainly to the new 3 '',6 ''-anhydroraffinose. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：929 / 935

页数：7

共 38 条

[1] ONE-STEP PREPARATION OF 6-PERFLUOROALKYLALKANOATES OF TREHALOSE AND SUCROSE FOR BIOMEDICAL USES [J].

ABOUHILALE, S ;

GREINER, J ;

RIESS, JG .

CARBOHYDRATE RESEARCH, 1991, 212 :55-64

[2] FORMATION OF 6-DEOXY-6-IODOHEXOPYRANOSIDES AS SUBSTRATES FOR THE HEX-5-ENOSE DEGRADATION [J].

ASPINALL, GO ;

CARPENTER, RC ;

KHONDO, L .

CARBOHYDRATE RESEARCH, 1987, 165 (02) :281-298

[3] Oligosaccharides in New Zealand honeydew honey [J].

Astwood, K ;

Lee, B ;

Manley-Harris, M .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (12) :4958-4962

[4] ORIGIN OF MELEZITOSE - BIOCHEMICAL RELATIONSHIP BETWEEN THE LIME TREE (TILIA SPP) AND AN APHIS (EUCALLIPTERUS-TILIAE L) [J].

BACON, JSD ;

DICKINSON, B .

BIOCHEMICAL JOURNAL, 1957, 66 (02) :289-297

[5] Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability [J].

Baker, IJA ;

Matthews, B ;

Suares, H ;

Krodkiewska, I ;

Furlong, DN ;

Grieser, F ;

Drummond, CJ .

JOURNAL OF SURFACTANTS AND DETERGENTS, 2000, 3 (01) :1-11

[6] Chromatographic analysis of sugars applied to the characterisation of monofloral honey [J].

Cotte, JF ;

Casabianca, H ;

Chardon, S ;

Lheritier, J ;

Grenier-Loustalot, MF .

ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2004, 380 (04) :698-705

[7] COMPARISON OF INTRAMOLECULAR HYDROGEN-BONDING CONFORMATIONS OF SUCROSE-CONTAINING OLIGOSACCHARIDES IN SOLUTION AND THE SOLID-STATE [J].

DAVIES, DB ;

CHRISTOFIDES, JC .

CARBOHYDRATE RESEARCH, 1987, 163 (02) :269-274

[8] Effect of carbohydrate fatty acid esters on Streptococcus sobrinus and glucosyltransferase activity [J].

Devulapalle, KS ;

de Segura, AG ;

Ferrer, M ;

Alcalde, M ;

Mooser, G ;

Plou, FJ .

CARBOHYDRATE RESEARCH, 2004, 339 (06) :1029-1034

[9] WHITE LAYER CAKE BATTER EMULSION CHARACTERISTICS - EFFECTS OF SUCROSE ESTER EMULSIFIERS [J].

EBELER, SE ;

BREYER, LM ;

WALKER, CE .

JOURNAL OF FOOD SCIENCE, 1986, 51 (05) :1276-1279

[10]

ELGLIS DT, 1925, J AM CHEM SOC, V47, P2724

← 1 2 3 4 →