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Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics.
Ushimaru, Richiro; Liu, Hung-Wen.
Afiliação
  • Ushimaru R; Department of Chemistry, and Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy , University of Texas at Austin , Austin , Texas 78712 , United States.
  • Liu HW; Department of Chemistry, and Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy , University of Texas at Austin , Austin , Texas 78712 , United States.
J Am Chem Soc ; 141(6): 2211-2214, 2019 02 13.
Article em En | MEDLINE | ID: mdl-30673214
ABSTRACT
Albomycins are peptidyl thionucleoside natural products that display antimicrobial activity against clinically important pathogens. Their structures are characterized by a thioheptose with atypical stereochemistry including a d-xylofuranose ring modified with a d-amino acid moiety. Herein it is demonstrated that AbmH is a pyridoxal 5'-phosphate (PLP)-dependent transaldolase that catalyzes a threo-selective aldol-type reaction to generate the thioheptose core with a d-ribofuranose ring and an l-amino acid moiety. The conversion of l-to d-amino acid configuration is catalyzed by the PLP-dependent epimerase AbmD. The d- ribo to d- xylo conversion of the thiofuranose ring appears according to gene deletion experiments to be mediated by AbmJ, which is annotated as a radical S-adenosyl-l-methionine (SAM) enzyme. These studies establish several key steps in the assembly of the thioheptose core during the biosynthesis of albomycins.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Ferricromo / Heptoses / Antibacterianos / Nucleosídeos Idioma: En Ano de publicação: 2019 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Ferricromo / Heptoses / Antibacterianos / Nucleosídeos Idioma: En Ano de publicação: 2019 Tipo de documento: Article