Efficient synthesis of phosphonodepsipeptides derived from norleucine

Autor:	Jiří Jiráček, Miloš Buděšínský, Miloslav Sanda, Pavel Fiedler, Ivona Hančlová, Jan Pícha, Václav Vaněk
Rok vydání:	2009
Předmět:	Stereochemistry Organic Chemistry Norleucine Synthon Biochemistry Phosphonate Chemical synthesis chemistry.chemical_compound chemistry Hydrogenolysis Drug Discovery Benzyl group Glycolic acid Derivative (chemistry)
Zdroj:	Tetrahedron. 65:6090-6103
ISSN:	0040-4020
DOI:	10.1016/j.tet.2009.05.051
Popis:	In the present work, we describe in detail an efficient solution synthesis of norleucine-derived phosphonopeptides mimicking the peptide sequences Nle-Gly(Ala) and Nle-Gly(Ala)-Val. The most efficient strategy involved use of the benzyl group. The synthesis was achieved through BOP-catalysed coupling of the monobenzyl ester of the N-Cbz-protected phosphonate derivative of norleucine with the hydroxyl moieties of derivatised l -lactic or glycolic acid. Subsequently, complete deprotection of the products was achieved in good yields by one-step Pd-catalysed hydrogenolysis. We also prepared the Fmoc-Nle-Ψ[PO(OH)O]-CH2-COOH synthon and demonstrated that this precursor is a suitable building block for the solid-phase synthesis of cysteine-containing phosphonopeptides.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f1e20c3ca45bc563a84170719b74fadd https://doi.org/10.1016/j.tet.2009.05.051 Zobrazit plný text záznamu Full Text from ScienceDirect