Preparation of Sugar Amino Acids by Claisen-Johnson Rearrangement: Synthesis and Incorporation into Enkephalin Analogues
Preparation of Sugar Amino Acids by Claisen-Johnson Rearrangement: Synthesis and Incorporation into Enkephalin Analogues
复制标题
通过克莱森-约翰逊重排制备糖氨基酸：合成并掺入脑啡肽类似物
DOI：
10.1002/ejoc.200400166
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发表时间：
2004
影响因子：
2.8
通讯作者：
B. Herradón
中科院分区：
文献类型：
--
作者：
Ana Montero;Enrique Mann;B. Herradón
我们已经开发了一种简便的路线，通过采用完全立体选择性的克莱森-约翰逊重排作为关键步骤来合成带有羧酸和氨基（以叠氮基掩蔽）的不饱和支链糖。几种在N-和C-末端具有不同取代模式的Met-和Leu-脑啡肽类似物是通过将这种糖氨基酸（SAA）作为母体五肽的中心Gly-Gly片段的替代物来制备的。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2004）
We have developed a convenient route for the synthesis of an unsaturated branched sugar bearing a carboxylic acid and an amino group (masked as an azide group) by employing a totally stereoselective Claisen−Johnson rearrangement as the key step. Several Met- and Leu-enkephalin analogues with different substitution patterns at the N- and C-termini were prepared by incorporating this sugar amino acid (SAA) as a substitute for the central Gly−Gly fragment of the parent pentapeptides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)