130883-96-4

Basic information

• Product Name: MCPA(S-Bzl)-D-Trp-Phe-Ile-Asn-Cys(Bzl)-Pro-Arg(Tos)-Gly-NH₂
• CAS NO: 130883-96-4
• Molecular Weight: 1481.87
• Mol File: 130883-96-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: MCPA(S-Bzl)-D-Trp-Phe-Ile-Asn-Cys(Bzl)-Pro-Arg(Tos)-Gly-NH₂(CAS DataBase Reference)
• NIST Chemistry Reference: MCPA(S-Bzl)-D-Trp-Phe-Ile-Asn-Cys(Bzl)-Pro-Arg(Tos)-Gly-NH₂(130883-96-4)
• EPA Substance Registry System: MCPA(S-Bzl)-D-Trp-Phe-Ile-Asn-Cys(Bzl)-Pro-Arg(Tos)-Gly-NH₂(130883-96-4)

Safety Data

• Hazardous Substances Data: 130883-96-4(Hazardous Substances Data)

Upstream product

• 13139-16-7 N-(tert-butyloxycarbonyl)-L-isoleucine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 55154-80-8 β-(benzylthio)-β,β-pentamethylenepropionic acid 
• 64905-10-8 Boc-D-Trp(For)-OH 

Downstream Products

• 130155-44-1 MCPA-D-Trp-Phe-Ile-Asn-Cys-Pro-Arg-Gly-NH2 

Relevant articles and documents

Design of potent oxytocin antagonists featuring D-tryptophan at position 2

We prepared nine analogues (1-9) of MCPA-D-Phe-Phe-Ile-Asn-Cys-Pro-Arg-Gly-NH2, [MCPA1,D-Phe2,Phe3, Ile4, Arg8]oxytocin (MCPA = β-mercapto-β,β-pentamethylenepropionic acid), a potent antagonist of the rat uterotonic action of oxytocin (OT). We replaced D-Phe with D-Trp and made [MCPA1,D-Trp2,Phe3,Ile4,Arg8]OT (1), which had OT pA2 of 7.51, somewhat higher than that of the D-Phe2 antagonist which has OT pA2 = 7.35 in our rat uterotonic assay. Both compounds are equipotent as antagonists of [Arg8]vasopressin in the rat antidiuretic assay, with pA2 = 8.1. Other substitutions gave [MCPA1,D-Trp2,4-Cl-Phe3,Ile4,Arg8]OT (2), OT pA2 7.44; [MCPA1,D-Trp2,Phe3,Ile4,3,4-dehydro-Pro7,Arg8]OT (3), OT pA2 = 7.42; [MCPA1,D-Trp2,Phe3,Arg8]OT (4), OT pA2 = 7.58; [MCPA1,D-Trp2,Phe3,Arg8,Gly9-NHEt]OT (5), OT pA2 = 7.49; [MCPA1,D-Trp2,Ile4,Arg8]OT (6), OT pA2 = 7.46; [MCPA1,D-Trp2,Val4,Arg8]OT (7), OT pA2 = 7.58; [MCPA1,D-Trp2,Thr4,Arg8]OT (8), pA2 = 7.48; and finally, [MCPA1,D-Trp2,Arg8]OT (9), which was a more potent and more selective OT antagonist, with OT pA2 = 7.77 in the uterotonic assay and ADH pA2 5.9 in the antidiuretic assay and hence is an important lead for the design of OT antagonists.