Synthesis of Novel Nonproteinogenic Amino Acids: N-Ethyl-α,β-dehydroamino Acid Methyl Esters
Synthesis of Novel Nonproteinogenic Amino Acids: N-Ethyl-α,β-dehydroamino Acid Methyl Esters
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新型非蛋白氨基酸的合成：N-乙基-α,β-脱氢氨基酸甲酯
DOI：
10.1002/ejoc.201001302
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发表时间：
2010
影响因子：
2.8
通讯作者：
A. C. Suárez
中科院分区：
文献类型：
--
作者：
L. Monteiro;Joanna Kołomańska;A. C. Suárez
本文介绍了以丝氨酸、苏氨酸和苯基丝氨酸为原料合成N-乙基-N-（4-硝基苯磺酰基）-α，β-脱氢氨基酸衍生物的两条路线。一条路线是在4-（二甲氨基）吡啶催化下，N-（4-硝基苯磺酰基）-β-羟基氨基酸酯与二叔丁基二环己基醚脱水，然后用四氟硼酸三乙基氧鎓盐对N-（4-硝基苯磺酰基）-α，β-脱氢氨基酸甲酯进行烷基化。第二种策略采用相同的程序，但顺序相反：烷基化，然后脱水。这些方法使得有可能首次获得新的非天然氨基酸，其包含N-乙基和α，β-β-氨基部分。
Two routes for the synthesis of N-ethyl-N-(4-nitrophenyl-sulfonyl)-α,β-dehydroamino acid derivatives from serine, threonine and phenylserine derivatives are presented. One route consists of dehydration of N-(4-nitrophenylsulfonyl)-β-hydroxyamino acid esters with di-tert-butyl dicarbonate catalyzed by 4-(dimethylamino)pyridine, followed by alkylation of the N-(4-nitrophenylsulfonyl)-α,β-dehydroamino acid methyl esters obtained with triethyloxonium tetrafluoroborate. The second strategy applied the same procedures but in inverse order: alkylation followed by dehydration. These methods made it possible to obtain for the first time, new non-natural amino acids, which incorporate both an N-ethyl and an α,β-dehydro moiety.