Solution and solid-phase synthesis of trifluoromethyl peptides and mimetics

This paper reviews the solution-phase synthesis of trifluoromethyl (Tfm)-analogues of bioactive peptides, such as RGD-peptides and the aspartyl protease inhibitor pepstatin, and the solution/solid-phase synthesis of Tfm-substituted retro- and retro-inverso peptides and hydroxamates.

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Bibliographic Details
Published in:	Journal of Fluorine Chemistry Vol. 112; no. 1; pp. 153 - 162
Main Authors:	Bravo, Pierfrancesco, Bruché, Luca, Pesenti, Cristina, Viani, Fiorenza, Volonterio, Alessandro, Zanda, Matteo
Format:	Book Review Journal Article
Language:	English
Published:	Elsevier B.V 2001
Subjects:	Asymmetric synthesis Peptides Peptidomimetics Solid-phase synthesis Trifluoromethyl group Boc, tert-butoxycarbonyl HOBt, 1-hydroxybenzotriazole Peptides EDCI, N-ethyl- N′-(3-dimethyl-aminopropyl)carbodiimide hydrochloride RP, reverse phase TIB, 1,1-bis-(trifluoroacetoxy)-iodobenzene NMM, N-methyl-morpholine Trifluoromethyl group Solid-phase synthesis DCC, dicyclohexylcarbodiimide HOAt, 1-hydroxy-7-azabenzotriazole GABOB, γ -amino-β-hydroxybutyric acid Bn, benzyl Cbz, carbobenzyloxy Asymmetric synthesis Peptidomimetics TMP, 2,4,6-trimethylpyridine ( sym-collidine) HATU, N, N, N′, N′-tetramethyl- O-(7-azabenzo-triazol-1-yl)uronium hexafluorophosphate DIC, diisopropylcarbodiimide AA, amino acid TFA, trifluoroacetic acid
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Description
Summary:	This paper reviews the solution-phase synthesis of trifluoromethyl (Tfm)-analogues of bioactive peptides, such as RGD-peptides and the aspartyl protease inhibitor pepstatin, and the solution/solid-phase synthesis of Tfm-substituted retro- and retro-inverso peptides and hydroxamates.
ISSN:	0022-1139 1873-3328
DOI:	10.1016/S0022-1139(01)00485-7