کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5222581 1383459 2009 14 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Efficient synthesis of phosphonodepsipeptides derived from norleucine
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Efficient synthesis of phosphonodepsipeptides derived from norleucine
چکیده انگلیسی

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.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 65, Issue 31, 1 August 2009, Pages 6090-6103
نویسندگان
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