Synthesis of N-Fmoc-O-(N′-Boc-N′-methyl)-aminohomoserine, an amino acid for the facile preparation of neoglycopeptides
Synthesis of N-Fmoc-O-(N′-Boc-N′-methyl)-aminohomoserine, an amino acid for the facile preparation of neoglycopeptides
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DOI：
10.1021/jo026641p
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发表时间：
2003-01-10
影响因子：
3.6
通讯作者：
Silva, O
中科院分区：
文献类型：
--
作者：
Carrasco, MR;Brown, RT;Silva, O
描述了从 L-高丝氨酸合成 N-Fmoc-O-(N'-Boc-N'-甲基)-氨基高丝氨酸，总产率为 35%。使用基于 Fmoc 化学的固相肽合成可以将该氨基酸有效地掺入肽中，并且可以在氨氧基侧链上对所得肽进行化学选择性糖基化以生成新糖肽。该衍生物的合成极大地扩展了先前开发的新糖肽合成策略的可用性。
The synthesis of N-Fmoc-O-(N'-Boc-N'-methyl)-aminohomoserine in 35% overall yield from L-homoserine is described. This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The synthesis of this derivative greatly expands the availability of a previously developed neoglycopeptide synthesis strategy.