Synthesis of the chlorofusin cyclic peptide: assignment of the asparagine stereochemistry.
An efficient synthesis of two diastereomers of the chlorofusin cyclic peptide bearing either the l-Asn3/d-Asn-4 or d-Asn3/l-Asn4 stereochemistry is detailed. Four key subunits were prepared, sequentially coupled, and cyclized to provide the two diastereomeric macrocycles. The absolute stereochemistry at the asparagine residues 3 and 4 was assigned as l and d, respectively, by correlating the NMR data of the two diastereomers with that reported for the natural product. [structure: see text]
Desai
Pankaj
P
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Pfeiffer
Steven S
SS
Boger
Dale L
DL
D000596:Amino Acids / Q000032:analysis; D001216:Asparagine / Q000737:chemistry*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D011487:Protein Conformation; D013237:Stereoisomerism
D000596:Amino Acids; D010456:Peptides, Cyclic; C434864:chlorofusin; D001216:Asparagine