N-ALPHA-FMOC-4-PHOSPHONO(DIFLUOROMETHYL)-L-PHENYLALANINE - A NEW O-PHOSPHOTYROSINE ISOSTERIC BUILDING-BLOCK SUITABLE FOR DIRECT INCORPORATION INTO PEPTIDES
N-ALPHA-FMOC-4-PHOSPHONO(DIFLUOROMETHYL)-L-PHENYLALANINE - A NEW O-PHOSPHOTYROSINE ISOSTERIC BUILDING-BLOCK SUITABLE FOR DIRECT INCORPORATION INTO PEPTIDES
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DOI：
10.1016/s0040-4039(00)78349-3
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发表时间：
1994-10-10
影响因子：
1.8
通讯作者：
GORDON, EM
中科院分区：
文献类型：
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作者：
GORDEEV, MF;PATEL, DV;GORDON, EM
描述了 N-α-Fmoc-4-膦酰基（二氟甲基）-L-苯丙氨酸 5 的有效制备方法。该磷酸酪氨酸电子等排体的合成涉及倒数第二个磷酸二乙酯中间体4的脱保护，其中BSTFA/TMS1是关键步骤。构件 5 可直接用于掺入肽中，无需保护侧链膦酸基团，如模型二氟膦肽 Ac-F(2)Pmy-Ile-Asn-Gln-NH2 和 Ac-Glu-F(2)Pmp-Ile-Asn-Gln-NH2 的有效制备所示。
An efficient preparation of N-alpha-Fmoc-4-phospono(difluoromethyl)-L-phenylalanine 5 is described. The synthesis of this phosphotyrosine isostere involves deprotection of the penultimate diethylphosphonate intermediate 4 with BSTFA/TMS1 as the key step. Building block 5 can be utilized directly for incorporation into peptides without protection of the side chain phosphonic acid group, as illustrated by the efficient preparation of model difluorophosphonopeptides Ac-F(2)Pmy-Ile-Asn-Gln-NH2 and Ac-Glu-F(2)Pmp-Ile-Asn-Gln-NH2.