When sugars form a hemiacetal ring, the carbonyl carbon atom becomes asymmetric, and the two diastereomers that result are called anomers. For example, D -glucose, a typical aldose, does not exist in a chain-like aldehyde form in aqueous solution, but forms a six-membered (pyranose) or five-membered (furanose) hemiacetal ring within the molecule (the former is the major product). In this case, an isomer in which the newly generated hydroxyl group is in a cis relationship with the hydroxyl group on the terminal (higher numbered) asymmetric carbon in the chain-like Fischer projection formula is called an α-anomer, and one in a trans relationship is called a β-anomer. In the α form, the six-membered ring is α- D -glucopyranose, and the five-membered ring is α- D -glucofuranose. These are in equilibrium with each other via the aldehyde form. In glycosides in which the hydroxyl group is replaced by an alkoxy group, these different ring isomers can be isolated individually, and the ring forms in the glycan are designated by the three-letter symbol (aldose [see alternative terminology]) with the addition of α or β (or pyranose (p) or planose (f) if necessary). Source: Morikita Publishing "Chemical Dictionary (2nd Edition)" Information about the Chemical Dictionary 2nd Edition |
糖がヘミアセタール環を形成することによってカルボニル炭素原子が不斉となり,その結果生じる二つのジアステレオマーをアノマーという.たとえば,代表的なアルドースであるD-グルコースは水溶液中で鎖状のアルデヒド形では存在せず,分子内で六員環(ピラノース),あるいは五員環(フラノース)のヘミアセタール環を形成している(前者が主生成物).その際,新しく生成したヒドロキシ基が,鎖状のフィッシャー投影式の末端の(番号の大きい)不斉炭素上のヒドロキシ基とシスの関係にある異性体をα-アノマー(α-anomer),トランスの関係にあるものをβ-アノマーとよぶ.α形では,六員環のものはα-D-グルコピラノース,五員環のものはα-D-グルコフラノースである.これらはアルデヒド形を経由して,相互に平衡関係にある.ヒドロキシ基がアルコキシ基に置換されたグルコシド類では,これらの異なる環形の異性体をそれぞれ単離することができ,糖鎖中の環形は三文字記号([別用語参照]アルドース)にα,β(必要ならば,ピラノース(p),プラノース(f)をつける)を追加して示される. 出典 森北出版「化学辞典(第2版)」化学辞典 第2版について 情報 |
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