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Galacturonic Acid Derivatives, VIII. Synthesis ofN-(D-Galacturonoyl) Amino Acids and Dipeptides

✍ Scribed by Vogel, Christian ;Jeschke, Udo ;Kramer, Sven ;Ott, Andrej-Jakob

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
729 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

D‐Galacturonic acid derivatives, amide‐linked to amino acids or dipeptides, have been synthesized. These glycoconjugates exhibit stability when the uronic acid residue is protected with isopropylidene and acetyl groups or is in its pyranoside form. The formation of the amide or peptide linkages was best achieved by the EDCI/HOBt coupling method; an alternative method employing the 1,2;3,4‐di‐O‐isopropylidene‐α‐D‐galactopyranuronosyl chloride 2 furnished only moderate yields of the conjugates. The use of NMR spectroscopy to detect racemization of the amino acid moiety is also discussed herein.

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