Norcystine, a New Tool for the Study of the Structure−Activity Relationship of Peptides

Norcysteine (Ncy) is an unnatural amino acid possessing an electronegative sulfur atom directly attached to the α-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.

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Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2006-05, Vol.8 (11), p.2361-2364
Hauptverfasser:	Samant, Manoj P, Rivier, Jean E
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino Acid Sequence Amino Acids - chemistry Cysteine - analogs & derivatives Cysteine - chemical synthesis Cysteine - chemistry Cystine - analogs & derivatives Cystine - chemistry Gonadotropin-Releasing Hormone - antagonists & inhibitors Gonadotropin-Releasing Hormone - chemistry Humans Luciferases - genetics Luciferases - metabolism Molecular Structure Peptides - chemical synthesis Peptides - chemistry Peptides - pharmacology Receptors, LHRH - metabolism Stereoisomerism Structure-Activity Relationship
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Beschreibung
Zusammenfassung:	Norcysteine (Ncy) is an unnatural amino acid possessing an electronegative sulfur atom directly attached to the α-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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol0606740