2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid, an amino acid for the synthesis of mimics of O-linked glycopeptides
2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid, an amino acid for the synthesis of mimics of O-linked glycopeptides
复制标题
DOI：
10.1002/bip.20496
复制
发表时间：
2006-01-01
期刊：
影响因子：
2.9
通讯作者：
Lee, FC
中科院分区：
文献类型：
--
作者：
Carrasco, MR;Brown, RT;Lee, FC
具有N-烷基氨基氧基侧链的氨基酸已被证明对快速合成新糖肽是有效的。还原糖与含有这些氨基酸的多肽的化学选择性反应提供了结构类似于它们的天然对应物的糖偶联物。2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic酸(Fmoc：9-荧甲氧基羰基；Boc：叔丁氧基)由Boc-Ser-OH总收率40%合成，并通过标准的Fmoc化学固相法合成多肽。得到的多肽被有效地糖基化，并作为O-连接的糖肽的模拟物。该衍生物的合成极大地扩展了N-烷基氨基氧基新糖肽策略的可用性。(C)2006年威利期刊公司。
Amino acids with N-alkylaminooxy side chains have proven effective for the rapid synthesis of neoglycopeptides. Chemoselective reaction of reducing sugars with peptides containing these amino acids provides glycoconjugates that are structurally similar to their natural counterparts. 2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid (Fmoc: 9-fluorenylmethoxycarbonyl; Boc: t-butyloxycarbonyl) was synthesized from Boc-Ser-OH in > 40% overall yield and incorporated into peptides by standard Fmoc chemistry based solid phase peptide synthesis. The resulting peptides are efficiently glycosylated and serve as mimics of O-linked glycopeptides. The synthesis of this derivative greatly expands the availability of the N-alkylaminooxy strategy for neoglycopeptides. (c) 2006 Wiley Periodicals, Inc.