Stereoselective synthesis of alpha-C-glucosyl serine and alanine via a cross-metathesis/cyclization strategy.
C-Glycosyl amino acids represent stable mimics of monomeric units within natural O-linked glycoproteins. Olefin cross-metathesis has been used to provide alkene precursors for a mercury(II)-mediated cyclization, yielding alpha-C-glucosyl serine and alanine.
Nolen
Ernest G
EG
Department of Chemistry, Colgate University, Hamilton, New York 13346, USA. enolen@mail.colgate.edu
Kurish
Adam J
AJ
Potter
Jennifer M
JM
Donahue
Lawrence A
LA
Orlando
Michael D
MD
D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006023:Glycoproteins / Q000138:chemical synthesis* / Q000737:chemistry*; D008628:Mercury / Q000737:chemistry; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D006023:Glycoproteins; D012694:Serine; D008628:Mercury; D000409:Alanine