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Verbesserte Synthese von N 1 ‐Pyridylthiaminpyrophosphat, einem coenzymatisch aktiven Analogon des Thiaminpyrophosphates
Author(s) -
Neef Holger,
Golbik Ralph,
Fahlbusch Barbel,
Schellenberger Alfred
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001167
Subject(s) - chemistry , pyrophosphate , yield (engineering) , stereochemistry , thiamine pyrophosphate , medicinal chemistry , cofactor , organic chemistry , materials science , metallurgy , enzyme
Improved Synthesis of N 1 ‐Pyridylthiamine Pyrophosphate, a Coenzymatically Active Analog of Thiamine Pyrophosphate Our previously published synthesis of the N 1 ‐pyridyl analog 1b of thiamine pyrophosphate 6) is improved resulting in a remarkably higher yield. Key reaction of this new synthetic pathway is the oxidative degradation of 5‐acetylpyridine 8 to the 5‐carboxylic acid 11 via the pyridinium compound 10 . Improved preparations of other intermediates are also described. The N 1 ‐pyridylthiamine pyrophosphate analog 1b has been separated and purified by ion exchange chromatography on Sephadex A‐25.