设计并合成一种试剂，用于将磷代苏氨酸类似物（2S,3R）-2-氨基-3-甲基-4-膦基丁酸（Pmab）以生物可逆的磷酰基-双-新戊酰氧甲基（POM）前药形式固相掺入肽中。
Design and synthesis of a reagent for solid-phase incorporation of the phosphothreonine mimetic (2S,3R)-2-amino-3-methyl-4-phosphonobutyric acid (Pmab) into peptides in a bio-reversible phosphonyl-bis-pivaloyloxymethyl (POM) prodrug form.
机构信息
Chemical Biology Laboratory, Molecular Discovery Program, Center for Cancer Research, National Cancer Institute-Frederick, National Cancer Institute, National Institutes of Health, Frederick, MD, 21702, USA.
出版信息
Amino Acids. 2013 Nov;45(5):1143-8. doi: 10.1007/s00726-013-1567-0. Epub 2013 Aug 2.
Abstract
Reported herein are the synthesis and solid-phase peptide incorporation of N-Fmoc-(2S,3R)-2-amino-3-methyl-4-phosphonobutyric acid bis-pivaloyloxymethyl phosphoryl ester [Fmoc-Pmab(POM)2-OH, 2] as a phosphatase-stable phosphothreonine (pThr) mimetic bearing orthogonal protection suitable for the synthesis of Pmab-containing peptides having bio-reversible protection of the phosphonic acid moiety. This represents the first report of a bio-reversibly protected pThr mimetic in a form suitable for facile solid-phase peptide synthesis.
摘要
本文报道了 N-Fmoc-(2S,3R)-2-氨基-3-甲基-4-膦酸基丁酸双-特戊酰氧甲基膦酸酯[Fmoc-Pmab(POM)2-OH，2]的合成和固相肽缩合，它是一种稳定的磷酸丝氨酸（pThr）模拟物，带有正交保护，适合合成具有生物可逆保护膦酸部分的 Pmab 肽。这是首例适合简便固相肽合成的生物可逆保护 pThr 模拟物的报道。
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