Untriakontapeptide with opiate activity

Abstract

An untriakontapeptide having significant opiate agonist activity has been isolated from camel pituitary glands. The structure of this peptide has been determined and this peptide was then synthesized utilizing solid phase peptide synthesis. Both natural and synthetic material show identical physical and biological properties.

I claim: 
     
       1. A compound of the formula Boc-Tyr(oBr-Z)-Gly-Gly-Phe-Met-Thr-Ser(Bzl)-Glu(OBzl)-Lys(oBr-Z)-Ser(Bzl)-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys(oBr-Z)-Asn-Ala-Ile Ile-Lys-(oBr-Z)-Asn-Ala-His(Boc)-Lys(oBr-Z)-Lys(oBr-X)-Gly-Gln® wherein oBr-Z is ortho bromobenzyloxycarbonyl; Bzl is benzyl; Boc is .[.toxycarbonyl.]. .Iadd.t-butyloxycarbonyl and ® is styrene-divinyl-benzene copolymer resin.     
     
     
       2. A compound of the formula H-tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-X-Lys-Asn-Ala-Y-Lys-Lys-Gly-Z-OH wherein X is Ile or Val; Y is His or Tyr and Z is Gln or Glu said compound being essentially free of other biogenic peptides.     
     
     
       3. The compound of claim .[.4.]. .Iadd.2 .Iaddend.wherein X is Ile; Y is His and Z is Gln. 
     
     
       4. The compound of claim 2 wherein X is Val; Y is His and Z is Gln. 
     
     
       5. The compound of claim 2 wherein X is Ile; Y is Tyr and Z is Glu. 
     
     
       6. A compound of the formula Boo-Tyr(oBr-Z)-Gly-Gly-Phe-Met-Thr-Ser(Bzl)-Glu(OBzl)-Lys-(oBr-Z)-Ser(BZl)-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys(oBr-Z)-Ans-Ala-Ile-Val-Lys-(oBr-Z)-Asn-Ala-His(Boc)-Lys(oBr-Z)-Lts(oBr-Z)-Glyn-Gln® wherein OBr-Z is orthobromobenzyloxycarbonyl; Bzl is benzyl; Boc is t-butyloxcarbonyl and ® is styrene-divinylbenzene copolymer resin.     
     
     
       7. A compound of the formula: Boc-Tyr(oBr-Z)-Gly-Gly-Phe-Me-Thr-Ser(Bzl)-Glu-(OBzl)-Lys-(oBr-Z)-Ser(Bzl)-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys(oBr-Z)-Asn-Ala-Ile-Ile-Lys-(oBrZ)-Asn-Ala-Tyr(oBr-Z)-Lys-(oBr-Z)-Lys(oBr-Z)-Gly-Glu(Bzl)® wherein oBr-Z is orthobromobenzyloxycarbonyl; Bzl is benzyl; Boc is t-butyloxycarbonyl and ® is styrene-divinylbenzene copolymer resin.