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Efficient synthesis of phosphonodepsipeptides derived from norleucine
- 1.0327520 - ÚOCHB 2010 RIV GB eng J - Journal Article
Pícha, Jan - Buděšínský, Miloš - Hančlová, Ivona - Šanda, Miloslav - Fiedler, Pavel - Vaněk, Václav - Jiráček, Jiří
Efficient synthesis of phosphonodepsipeptides derived from norleucine.
Tetrahedron. Roč. 65, č. 31 (2009), s. 6090-6103. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA ČR GA203/06/1405; GA MŠMT(CZ) LC06077
Institutional research plan: CEZ:AV0Z40550506
Keywords : phosphonate * pseudopeptide * inhibitor * synthesis * norleucine
Subject RIV: CC - Organic Chemistry
Impact factor: 3.219, year: 2009
In the present work, we describe synthesis of phosphonopeptides mimicking the peptide sequences Nle-Gly(Ala) and Nle-Gly(Ala)-Val. 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.
Permanent Link: http://hdl.handle.net/11104/0174312
Number of the records: 1