Pseudoglycosyltransferase Catalyzes Nonglycosidic C-N Coupling in Validamycin A Biosynthesis

被引：22

作者：

Asamizu, Shumpei ^{[1
]}

Yang, Jongtae ^{[1
]}

Almabruk, Khaled H. ^{[1
]}

Mahmud, Taifo ^{[1
]}

机构：

[1] Oregon State Univ, Dept Pharmaceut Sci, Corvallis, OR 97331 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 31期

关键词：

HYGROSCOPICUS VAR. LIMONEUS; GENE-CLUSTER; GLYCOSYLTRANSFERASE;

D O I：

10.1021/ja203574u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented nonglycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated 'pseudoglycosyltransferase' catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7'-phosphate with net retention of the 'anomeric' configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7'-phosphate to validoxylamine A.

引用

页码：12124 / 12135

页数：12

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