کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5226662 1383582 2006 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Regioselectivity in acylation of oligosaccharides catalyzed by the metalloprotease thermolysin
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Regioselectivity in acylation of oligosaccharides catalyzed by the metalloprotease thermolysin
چکیده انگلیسی

Investigation of the acylation scope of carbohydrates by metalloprotease thermolysin immobilized on Celite as biocatalyst has been carried out. The reactions were performed in DMSO, a good solvent for carbohydrates, where the enzyme has previously shown its activity in transesterifications of sucrose, maltose and maltose-containing oligosaccharides. Surprisingly, no reaction was observed for glucose or the glucose-containing disaccharides, trehalose and lactose. In contrast, laurate monoesters of several sucrose-containing tri- and tetrasaccharides were synthetized through a one step transesterification using vinyl laurate as the acylating agent. Enzyme regioselectivity was accurately determined by HPLC/MS and the structure of the main regioisomers was established by a combination of NMR experiments. The preferred position of acylation in all cases was the 2-OH of the α-d-glucopyranose moiety linked 1→2 to the β-d-fructofuranose unit. These results correlate with the regioselectivity observed in the case of the disaccharide sucrose. A general carbohydrate binding motif for catalysis by thermolysin is proposed.

Graphical Abstract

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 62, Issue 10, 6 March 2006, Pages 2361-2369
نویسندگان
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