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Glucose‐Based AB 2 ‐Building Blocks for the Construction of Branched Glycopeptidomimetics
Author(s) -
Kieburg Christoffer,
Sadalapure Kashinath,
Lindhorst Thisbe K.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200006)2000:11<2035::aid-ejoc2035>3.0.co;2-v
Subject(s) - chemistry , glycan , glycosylation , peptide , combinatorial chemistry , carbohydrate , coupling (piping) , carbohydrate chemistry , biochemistry , glycoprotein , mechanical engineering , engineering
Glycopeptido derivatives are attractive oligosaccharide mimetics which allow the use of peptide‐coupling reactions for the assembly of carbohydrate units instead of the more difficult glycosylation procedures. Moreover, glycopeptidomimetics are attractive as synthetic ligands for carbohydrate‐specific molecular recognition. With regard to the multiantennary nature of the naturally occurring N ‐glycans, we synthesized the orthogonally protected glucose‐based AB 2 ‐building blocks 1 and 2 , which allow the assembly of branched glycopeptidomimetics by peptide‐coupling reactions. This was exemplified by the synthesis of multivalent glycopeptidomimetics 14 and 15 derived therefrom.