Premium
3‐ C ‐Hydroxymethyl‐ D ‐riburonic Acid Synthesis of the Branched‐Chain Uronic Acid and comparison with a carbohydrate component of a naturally occurring bilirubin conjugate
Author(s) -
Blackstock Walter P.,
Kuenzle Clive C.,
Eugster Conrad H.
Publication year - 1974
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19740570406
Subject(s) - chemistry , uronic acid , hydroxymethyl , carbohydrate , conjugate , natural product , glycoside , chromatography , stereochemistry , organic chemistry , polysaccharide , mathematical analysis , mathematics
A novel carbohydrate has previously been isolated from human bile as a complex glycoside of bilirubin [1]. This compound has been tentatively identified as 3‐ C ‐hydroxymethyl‐ D ‐riburonic acid. To test this structural assignment the proposed branched‐chain uronic acid was synthesized. Gas chromatographic and mass spectrometric comparison of the natural and synthetic materials indicated that the proposed structure, 3‐C‐hydroxymethyl‐D‐riburonic acid, did not apply to thc natural product.