Conformationally restricted glutamic acid analogues: stereoisomers of 1-aminospiro[3.3]-heptane-1,6-dicarboxylic acid.

Мова статті: 
Англійська
Автор(и) статті: 
Anton V. Chernykh, Dmytro S. Radchenko, Oleksandr O. Grygorenko, Dmitriy M. Volochnyuk, Svitlana V. Shishkina, Oleg V. Shishkin, Igor V. Komarov.
Вихідні данні статті: 
RSC Adv., 2014,4, 10894-10902
Назва журналу: 
RSC Advances
Рік публікації: 
2014
Volume: 
4
Ключові слова: 
glutamic acid analogues, stereoisomers
Ключове слово: 
glutamic acid analogues,
Ключове слово: 
stereoisomers
Impact Factor: 
3.708
All four stereoisomers of the title compound (1a–d) were prepared, starting from a common precursor, 3-oxocyclobutanecarboxylic acid. Lewis acid-catalyzed rearrangement of a 8-oxadispiro[2.0.3.1]octane-6-carboxylic acid derivative was used as the key synthetic step to construct the suitably functionalized spiro[3.3]heptane skeleton. A stabilized oxaphosphetane intermediate of the Wittig reaction was detected along the synthetic route. Separation of the diastereomeric intermediates allowed each target compound to be obtained as a single stereoisomer. The target compounds are all analogues of the glutamic acid; they mimic glutamate in a large array of restricted conformations, which might be used in mechanistic studies or in a systematic search for biologically active compounds.
Назва підрозділу: 
Кафедра супрамолекулярної хімії та біохімії
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Дизайн: Інститут високих технологій
Ivan Ivanov