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Efficient Chemical Synthesis of the Two Anomers of ADP‐ L ‐ glycero‐ and D ‐ glycero‐ D ‐ manno ‐Heptopyranose Allows the Determination of the Substrate Specificities of Bacterial Heptosyltransferases
Author(s) -
Zamyatina Alla,
Gronow Sabine,
Oertelt Clemens,
Puchberger Michael,
Brade Helmut,
Kosma Paul
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001117)39:22<4150::aid-anie4150>3.0.co;2-a
Subject(s) - anomer , substrate (aquarium) , chemistry , nucleotide , derivative (finance) , stereochemistry , combinatorial chemistry , coupling (piping) , biochemistry , biology , materials science , financial economics , economics , gene , metallurgy , ecology
By simply inverting the coupling and deprotection step, anomeric ADP‐ L ‐ glycero ‐ and D ‐ glycero ‐ D ‐ manno ‐heptopyranoses can be obtained in high yields. Only the β ‐configured sugar nucleotides (the L ‐ glycero ‐ D ‐ manno derivative is shown), which may serve as novel lead structures in antibacterial drug design, were substrates for bacterial heptosyltransferases from E. coli. Kdo=3‐deoxy‐ D ‐ manno ‐oct‐2‐ulosonic acid.