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Мутаротация

Мутаротация (от лат. muto — изменяю и rotatio — вращение) — изменение величины оптического вращения растворов оптически активных соединений вследствие взаимного перехода аномеров вещества друг в друга. В химии углеводов под мутаротацией обычно подразумевается эпимеризация полуацетального атома углерода[1]. Характерна для моносахаридов, восстанавливающих олигосахаридов, лактонов и др. Мутаротация может катализироваться кислотами и основаниями.

Явление открыл в 1846 году Огюстен-Пьер Дюбрёнфо[англ.]. Термин «мутаротация» предложил Томас Мартин Лоури.

Мутаротация глюкозы

В случае глюкозы мутаротация объясняется установлением равновесия: в равновесном состоянии присутствует 36 % aльфа-формы и 64 % бета-формы. Промежуточная альдегидная форма содержится в ничтожно малой концентрации. Преимущественное образование β-формы объясняется тем, что она более термодинамически стабильна.

Примечания

  1. mutarotation // IUPAC Gold Book. Дата обращения: 1 декабря 2007. Архивировано 25 февраля 2015 года.

Литература

  • Потапов В. Стереохимия. — 2-е издание. — 1988.

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