A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid

被引:44
作者
Clausen, MH [1 ]
Jorgensen, MR [1 ]
Thorsen, J [1 ]
Madsen, R [1 ]
机构
[1] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 05期
关键词
D O I
10.1039/b006981g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of monomethyl-esterified trigalacturonans 1-3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycosyl donors and acceptors using the n-pentenyl glycosylation technique. Yields of the desired alpha -anomers were in the 50 to 74% range. The trigalactans thus obtained were then subjected to oxidation at C-6. Depending on the protecting group at this position the oxidation either produced the carboxylic acid or the corresponding methyl ester. Hereby, oligomers of galacturonic acid can be prepared with methyl esters introduced in a regiocontrolled fashion.
引用
收藏
页码:543 / 551
页数:9
相关论文
共 27 条
[1]   Kinetic characterization of Aspergillus niger N400 endopolygalacturonases I, II and C [J].
Benen, JAE ;
Kester, HCM ;
Visser, J .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1999, 259 (03) :577-585
[2]   CHLOROACETYL GROUP IN SYNTHETIC CARBOHYDRATE CHEMISTRY [J].
BERTOLINI, M ;
GLAUDEMANS, CP .
CARBOHYDRATE RESEARCH, 1970, 15 (02) :263-+
[3]   C-13 NUCLEAR MAGNETIC-RESONANCE DATA FOR OLIGOSACCHARIDES [J].
BOCK, K ;
PEDERSEN, C ;
PEDERSEN, H .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1984, 42 :193-225
[4]   Nature of sites hydrolyzable by endopolygalacturonase in partially-esterified homogalacturonans [J].
Chen, EMW ;
Mort, AJ .
CARBOHYDRATE POLYMERS, 1996, 29 (02) :129-136
[5]   Analysis of partially methyl-esterified galacturonic acid oligomers by high-performance anion-exchange chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry [J].
Daas, PJH ;
Arisz, PW ;
Schols, HA ;
De Ruiter, GA ;
Voragen, AGJ .
ANALYTICAL BIOCHEMISTRY, 1998, 257 (02) :195-202
[6]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[7]   AN IMPROVEMENT IN THE PREPARATION OF SOME CARBOHYDRATE BENZYLIDENE ACETALS [J].
FERRO, V ;
MOCERINO, M ;
STICK, RV ;
TILBROOK, DMG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (05) :813-815
[8]  
FRASERREID B, 1992, SYNLETT, P927
[9]  
HASHIMOTO N, 1981, CHEM PHARM BULL, V29, P1475
[10]   Tandem mass spectrometric analysis of Aspergillus niger pectin methylesterase:: mode of action on fully methyl-esterified oligogalacturonates [J].
Kester, HCM ;
Benen, JAE ;
Visser, J ;
Warren, ME ;
Orlando, R ;
Bergmann, C ;
Magaud, D ;
Anker, D ;
Doutheau, A .
BIOCHEMICAL JOURNAL, 2000, 346 (02) :469-474