Alkylated sugar amino acids: a new entry toward highly functionalized dipeptide isosters.
[reaction: see text] Novel highly functionalized dipeptide isosters are synthesized via a diastereoselective alkyl/arylation protocol of a glucose-derived (R)-tert-butanesulfinylimine. One of these novel sugar amino acid derivatives, a D-Ala-Ser/Thr isostere, was applied in a peptide synthesis protocol to afford a cyclic tetramer.
Raunkjaer
Michael
M
Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
El Oualid
Farid
F
van der Marel
Gijs A
GA
Overkleeft
Herman S
HS
Overhand
Mark
M
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013400:Sugar Acids / Q000737:chemistry*
D000596:Amino Acids; D004151:Dipeptides; D007202:Indicators and Reagents; D010456:Peptides, Cyclic; D013400:Sugar Acids