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Thymidine Diphospho‐6‐deoxy‐α‐ D ‐ ribo ‐3‐hexulose—Synthesis of a Central Intermediate in the Biosynthesis of Di‐ and Trideoxysugars
Author(s) -
Müller Thomas,
Schmidt Richard R.
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199513281
Subject(s) - biosynthesis , thymidine , chemistry , stereochemistry , ozonolysis , sugar , photoaffinity labeling , biochemistry , methylene , linkage (software) , organic chemistry , gene , binding site , dna
An indirect strategy was needed for the first synthesis of a labile dNDP‐3‐keto sugar, the title compound 2 . D ‐Glucose is converted into methylene phosphate 1 , which after ozonolysis and linkage of thymidine monophosphate, provides 2 . According to present knowledge the target compound is an important intermediate in the biosynthesis of dideoxy, trideoxy, aminodeoxy, and branched sugars.