title: [Synthesis of cyclo-[des(1,2-L-alanyl-glycine, 14-L-cysteine)-3-s-carboxymethyl-L-homocysteinamid, 8-D-tryptophan]-somatostatin].
abstract: The authors describe the synthesis of a shorter-chained somatostatin analogue in which the ring size of the native molecule is largely preserved by incorporation of S-carboxymethyl-L-homocysteinamid and ring closure via its side-chain function. This synthesis involves the linkage of Boc-Phe-D-Trp-Lys[Z(pCl)]-Thr-Phe-Thr-Ser-OH to H-Hcy(CH2-CO-Lys[Z(oCl)]-Asn-Phe-OMe)-NH2 and subsequent azide cyclization. In contrast to somatostatin, the somatostatin analogue thus obtained produces, when applied intracerebroventricularly to rats, a decrease in the dopamine content of the striatum.
mesh_terms: D000818:Animals; D001923:Brain Chemistry / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D004298:Dopamine / Q000378:metabolism; D007276:Injections, Intraventricular; D051381:Rats; D013004:Somatostatin / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D013004:Somatostatin; C037189:somatostatin, cyclo(des-Ala(1)-des-Gly(2)-S-COMe-homo-CysNH2(3)-Trp(8)-des-Cys(14))-; D004298:Dopamine
vernacular_title: Synthese von cyclo-[Des(1,2-L-alanyl-glycin, 14-L-Cystein)-3-S-carboxymethyl-L-homocysteinamid, 8-D-Tryptophan]-somatostatin.