6-O-(10-Undecylenoyl)-D-Glucose: Controlled Enzymatic Synthesis and Structure Elucidation by 1H and 13C NMR

Autor: Wu Yue, Ping Jia Yao, Yua Nan Wei, Qun Liang Li, Yin Zhen Wang
Rok vydání: 2011
Předmět:
Zdroj: Advanced Materials Research. :1318-1324
ISSN: 1662-8985
Popis: A direct esterification synthesis of glucose undecylenic acid sugar monoester is described, using the immobilized lipase enzyme NOVO-435 in 2-methyl-2-butonal and in ethyl methyl ketone (EMK). conditions were optimized in order to produce the monoester more rapidly and in higher yield. After the reaction product was purified, mass spectroscopy revealed that it had a molecular weight of 346.2 AMU. Further characterization by 1H and 13C NMR spectroscopy was carried out, including two-dimensional (2D) 1H-1H COSY and heteronuclear 1H-13C HSQC experiments. These data enabled identification of the monoester product to be 6-O-(10-undercylenoyl)α-D-glucose (74%), and 6-O-(10-undercylenoyl)β-D-glucose (26%) in methanol solution.
Databáze: OpenAIRE