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

Yin Zhen Wang; Qun Liang Li; Wu Yue; Ping Jia Yao; Yua Nan Wei

doi:10.4028/www.scientific.net/AMR.396-398.1318

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HomeAdvanced Materials ResearchAdvanced Materials Research Vols. 396-3986-O-(10-Undecylenoyl)-D-Glucose: Controlled...

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

Abstract:

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.

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Advanced Materials Research (Volumes 396-398)

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1318-1324

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https://doi.org/10.4028/www.scientific.net/AMR.396-398.1318

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Online since:

November 2011

Authors:

Yin Zhen Wang, Qun Liang Li, Wu Yue, Ping Jia Yao, Yua Nan Wei

Keywords:

6-O-(10-Undercylenoyl)α-D-Glucose, Immobilized Lipase, Monoester, NMR Spectroscopy

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