Synthesis of model glycolipids having two long alkyl chains

✍ Scribed by Zhongzhi Zhang; Kimitoshi Fukunaga; Toshimi Shimizu; Katsumi Nakao

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 148 KB
• Volume: 277
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00298-8

✦ Synopsis

Some transesterifications and hydrolyses have been successfully carded out in organic solvent with enzymes modified by the detergent didodecyl glucosyl glutamate. The stability and reaction activity of the enzymes used are strongly dependent on the type and structure of the detergents. Nonionic detergents were considered to be the most useful for modification of enzymes [1][2][3][4][5]. The present investigation has aimed at the synthesis of glycolipids having an amino acid residue interposed between the hydrophilic moiety and hydrophobic double-chain segment as a hydrogen-bonding component to constitute a morphologically stable bilayer membrane [6].

Generally, diethyl phosphocyanidate (DEPC) [7] is considered to be a good coupling reagent between an acid and amine and has been used for example to catalyze the formation of N-substituted lactobionamides from amines and lactobionic acid. However, DEPC was found to make a minor contribution to this condensation reaction, as well as N, N'-dicyclohexylcarbodiimide (DCC) [8].

Although lactobionic acid is readily converted into lactonolactone, the condensation of the lactonolactone with the amino groups of dialkyl L-glutamate is not possible, perhaps due to steric hindrance of two alkyl chains of dialkyl L-glutamate. We have selected p-aminomethylbenzoic acid in order to condense the oligosaccharide containing carboxyl group and the dialkyl L-glutamate under the action of DEPC in a final reaction