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Approaches to Pyranuronic β‐Sugar Amino Acid Building Blocks of Peptidosaccharide Foldamers
Author(s) -
Goldschmidt Gőz Viktória,
Pintér István,
Harmat Veronika,
Perczel András
Publication year - 2018
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/ejoc.201701612
Subject(s) - chemistry , oxime , epimer , combinatorial chemistry , peptide synthesis , amino acid , biocompatible material , peptidomimetic , total synthesis , sugar , peptide , organic chemistry , biochemistry , biomedical engineering , medicine
Pyranuronic β‐sugar amino acids (β‐SAAs) are biocompatible and tuneable building blocks of foldamers and chimera‐peptides. The scalable and economical total synthesis of two building blocks is described here. These C‐4 epimers, Fmoc‐GlcAPU(Me)‐OH ( 7 ) and Fmoc‐GalAPU(Me)‐OH ( 8 ), which are suitable for solid phase peptide synthesis, were prepared via a common oxime intermediate 16 . The new synthesis uses nine consecutive steps, starting from methyl α‐ d ‐glucopyranoside ( 6 ). The synthesis is fine‐tuned, optimized, and ready for large‐scale and cost‐efficient production.