NDLI: Synthesis of [1, 6-cyclo(Acetyl-1-L-glutamic acid, 2-D-phenylalanine, 3-D-tryptophan, 6-D-lysine)] luteinizing hormone-releasing hormone on poly-N-acrylylpyrrolidine resin

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Synthesis of [1, 6-cyclo(Acetyl-1-L-glutamic acid, 2-D-phenylalanine, 3-D-tryptophan, 6-D-lysine)] luteinizing hormone-releasing hormone on poly-N-acrylylpyrrolidine resin

Content Provider	Scilit
Author	Smith, Clark W. Skala, Gerald Wilks, John W.
Copyright Year	2009
Description	Journal: International journal of peptide and protein research The protected peptide, Ac-Glu(OBut)-D-Phe-D-Trp-Ser(But)-Tyr(But)-D-Lys (Z)-Leu-Arg(Tos)-Pro-Gly-NH2 was synthesized in a stepwise manner on a resin of poly-N-acrylylpyrrolidine using both acid cleavable N alpha-tert.-butyloxycarbonyl and base cleavable N alpha-fluorenylmethyloxycarbonyl protecting groups. After cleavage by ammonolysis in methanol, the tert.-butyl and benzyloxy-carbonyl side-chain protecting groups were cleaved with CF3-CO2H-thioanisole and the 1-6 amide ring formed by cyclization with diphenylphosphorylazide, after which the remaining tosyl protecting group was cleaved in HF-anisole. [1,6-Cyclo(Ac-Glu1, D-Phe2, D-Trp3, D-Lys6]LH-RH exhibited less than 10% of the antiovulatory potency of [D less than Glu1, D-Phe2, D-Trp3,6] LH-RH, a potent linear antagonist.
Ending Page	134
Starting Page	127
ISSN	2573508X
DOI	10.1111/j.1399-3011.1983.tb03086.x
Journal	International journal of peptide and protein research
Issue Number	2
Volume Number	21
Language	English
Publisher	Wiley-Blackwell
Publisher Date	2009-01-12
Access Restriction	Open
Subject Keyword	Journal: International journal of peptide and protein research Biologically Active Conformation Luteinizing Hormone‐releasing Hormone Polyamide Support Solid Phase Peptide Synthesis
Content Type	Text
Resource Type	Article

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