Synthesis of new amino acids with a 5-imino-2,5-dihydro-3-furanyl substituent at the amino group

被引：12

作者：

Trofimov, Boris A.

Mal'kina, Anastasiya G.

Shemyakina, Olesya A.

Borisova, Angela P.

Nosyreva, Valentina V.

Dyachenko, Oleg A.

Kazheva, Olga N.

Alexandrov, Germadii G.

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia

[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Russia

[3] Russian Acad Sci, NS Kurnakov Inst Gen & Inorgan Chem, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2007年 / 17期

关键词：

amino acids; acetylenes; nitriles; 2,5-dihydrofurans; nucleophilic addition;

D O I：

10.1055/s-2007-983819

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amino acids (glycine, P-alanine, gamma-aminobutyric and epsilon-animocapronic acids, D,L-valine, and D,L-leucine) react under biomimetic conditions (H2O, NaOH, pH similar to 8.6-9.9, room temperature) smoothly with alpha,beta-acetylenic gamma-hydroxyacid nitriles to give a novel family Of unnatural amino acids containing a 5-imino-2,5-dihydro-3-furanyl substituent at the amino group, in 61-98% yield. As follows from a single-crystal X-ray analysis of 2-[(5-imino-2,2dimethyl-2.5-dihydro-3 -furanyl)amino] acetic acid, the synthesized amino acids are zwitterions with a protonated imino group in the iminodihydrofuran rnoiety.

引用

页码：2641 / 2646

页数：6

共 43 条

[1] The bogorol family of antibiotics: Template-based structure elucidation and a new approach to positioning enantiomeric pairs of amino acids [J].