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- Title
Synthesis of a New Bivalent Hirudin Analog (hirufos), which includes a stable 4′-phosphono- L-phenylalanine mimic of ( L-tyrosine O<sup>4</sup>-sulfate)-63.
- Authors
Thurieau, Christophe; Guyard, Christel; Simonet, Serge; Verbeuren, Tony J.; Fauchère, Jean-Luc
- Abstract
The synthesis on solid phase of a new derivative of the anticoagulant protein hirudin is described (see Scheme and Fig.1, I). The henicosapeptide is a bivalent conjugate of the C-terminus of hirudin and of the active-site-binding tetrapeptide D-Phe-Pro-Arg-Pro linked via a tetraglycine spacer. The peptide, for which the name hirufos was coined, incorporates a stable phosphono derivative of L-phenylalanine which, combined with the other structural modifications, leads to a potent anticoagulant agent. Synthesis was readily achieved by the (9 H-fluoren-9-yl)-methoxycarbonyl (Fmoc) strategy followed by acidolytic cleavage from the resin and deprotection, including the liberation of the crucial phosphonic group on L-phenylalanine.
- Publication
Helvetica Chimica Acta, 1994, Vol 77, Issue 3, p679
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19940770311