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Carbohydrate chemistry: monosaccharides and their oligomers by Hassan Saad El Khadem

By Hassan Saad El Khadem

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And the OH up, and the β anomer has C-l, ( 5 ) , and the OH down. (d) Assigning an a or β configuration to a 2-ketose, or representing a ketose anomer using a Haworth formula, may seem confusing. The easi­ est way is simply to draw the anomeric OH group in the same direction (up or down) as in the corresponding aldose anomer and then replace the anomeric hydrogen atom of the latter with CH 2OH. When this is done, the β anomer will have acquired the same (R) or ( 5 ) configuration as the last chiral center (C-5 of an aldohexose), and the a anomer will have acquired the opposite configuration.

IH-NMR spectra ofa solution of a-D-glucose in Me2S0-d6 at 400 MHz. (a) OH protons coupled; (b) OH protons decoupled. 30 2. Structure, Configuration, and Conformation of M o n o s a c c h a r i d e s mixture of at least two (a and β ) furanoses and two ( a and β) pyranoses, as well as possibly traces of the acyclic form and its hydrate. In addition, a and β septanose forms may exist, but they are not detectable with aldoses. 4 Usually, the two furanose forms are favored kinetically, whereas the two pyranose forms are favored thermodynamically and therefore pre­ ponderate at equilibrium.

The six-membered ring produced in the second case is related to tetrahydropyran and is called pyranose. Because cyclization converts an achiral aldehyde carbon atom into a chiral hemiacetal carbon atom, two isomers, termed anomers, are produced; these are designated a and jS. 00 1600 Frequency (cm Fig. 4. 1400 _1 1200 1000 ) Infrared spectrum of crystalline j3-D-glucopyranose (KBr). 100 lOa 400 200 H HO H H H-S (a) I In. -;;;J}J JJ~l IJVL h) '-l> (b) 6 5 b 4 3 Fig. s. IH-NMR spectra ofa solution of a-D-glucose in Me2S0-d6 at 400 MHz.

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