Norcystine, a new tool for the study of the structure-activity relationship of peptides.
[reaction: see text] Norcysteine (Ncy) is an unnatural amino acid possessing an electronegative sulfur atom directly attached to the alpha-carbon atom. We describe the synthesis of Boc-D,L-Ncy(Mob)-OH, the resolution of its methyl ester, and the introduction of both D- and L-Ncy in GnRH analogues.
Samant
Manoj P
MP
The Clayton Foundation Laboratories for Peptide Biology, The Salk Institute, La Jolla, California 92037, USA.
Rivier
Jean E
JE
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003553:Cystine / Q000031:analogs & derivatives* / Q000737:chemistry*; D007987:Gonadotropin-Releasing Hormone / Q000037:antagonists & inhibitors / Q000737:chemistry*; D006801:Humans; D008156:Luciferases / Q000235:genetics / Q000378:metabolism; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011966:Receptors, LHRH / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000596:Amino Acids; C517694:Boc-D,L-Ncy(Mob)-OH; D010455:Peptides; D011966:Receptors, LHRH; D007987:Gonadotropin-Releasing Hormone; D003553:Cystine; D008156:Luciferases; D003545:Cysteine