SYNTHESIS OF RGD ANALOGS CONTAINING ALPHA-TFM-ARGININE AS POTENTIAL FIBRINOGEN RECEPTOR ANTAGONISTS

Authors
DALPOZZO A MUZI L MORONI M RONDANIN R DECASTIGLIONE R BRAVO P ZANDA M
Citation
A. Dalpozzo et al., SYNTHESIS OF RGD ANALOGS CONTAINING ALPHA-TFM-ARGININE AS POTENTIAL FIBRINOGEN RECEPTOR ANTAGONISTS, Tetrahedron, 54(22), 1998, pp. 6019-6028
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
22
Year of publication
1998
Pages
6019 - 6028
Database
ISI
SICI code
0040-4020(1998)54:22<6019:SORACA>2.0.ZU;2-K
Abstract
The synthesis of two peptide mimetics of RGD, alpha-Tfm-Arg-Gly-Asp-Ph e-NH2 9 and alpha-Tfm-Arg-Gly-Asp-NH-(CH2)(2)-C6H5 13, is described. T he precursor of alpha-Tfm-ornithine was obtained in two synthetic step s from 2-N-Cbz-2-Tfm-hexanediacid-1-alkyl ester and introduced into th e peptide chain by alpha-carboxy-group activation via oxazolone. The i ntroduction of the guanidine residue led to the final peptides as mixt ures of the two diastereomers. Configurationally pure peptides were ob tained in good yields by RP-HPLC. (C) 1998 Elsevier Science Ltd. All r ights reserved.