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Synthesis of 5-aminopentyl 4,6-O-[(R)-1-carboxyethylidene]-β-d-galactopyranoside and its use as a ligand for the affinity chromatography of human serum amyloid P protein

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
253
Identifiers
DOI: 10.1016/0008-6215(94)80063-4
Disciplines
  • Biology

Abstract

Abstract A series of 2,3-di- O-benzoyl- d-galactopyranosides, α-allyl ( 5), α-benzyl ( 6), β-ethyl-1-thio ( 7), β-phenyl-1-thio ( 8), and α-methyl ( 9), were prepared from the corresponding 4,6- 0-benzylidene derivatives and were acetalated in acetonitrile with methyl pyruvate, to give diastereoselectively the 2,3-di- O-benzoyl-4,6- O-[( R)-1-methoxycarbonylethylidene]- d-galactopyranosides 10–16. The latter were converted into the 2,3-di- O-benzoyl-4,6- O-[( R)-1-methoxycarbonylethylidene]- d-galactopyranosyl α- and β-trichloroacetimidates 19 and 20, α- and β-fluorides 21 and 22, the α-bromide 23, and the α-chloride 24, respectively. These donors, including the phenyl 1-thiogalactoside 14, reacted with 5-[(benzyloxycarbonyl)amino]pentanol to give the corresponding protected β- d-galactoside 27, deblocking of which afforded the title compound 1. Binding of 1 to epoxypropyl-modified acrylamide beads gave an affinity adsorbent that was used to isolate serum amyloid P protein from human serum.

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