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

By Hassan Saad El Khadem

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A particular conformation is designated by the same method for furanoses and pyranoses. Here, the letter used to designate the form (for example, Ε or T) is preceded by the number of the ring atom situated above the plane of the ring and is followed by the number of the ring atom below the plane of the ring; a ring oxygen atom is designated O. , Γ 3 . It may be noted that, as the envelope forms have only one atom above or below the ring, the letter Ε is accompanied by one number only. The two 2 envelope forms °E and E0 and the twist form Γ 3 are depicted.

Here, the letter used to designate the form (for example, Ε or T) is preceded by the number of the ring atom situated above the plane of the ring and is followed by the number of the ring atom below the plane of the ring; a ring oxygen atom is designated O. , Γ 3 . It may be noted that, as the envelope forms have only one atom above or below the ring, the letter Ε is accompanied by one number only. The two 2 envelope forms °E and E0 and the twist form Γ 3 are depicted. 46 2. Structure, Configuration, and Conformation of Monosaccharides Envelope forms 1 E ; E ^ Possible envelope forms (10): 2 3 4 Ε ; E 2 ; Ε; E 3; E ; E 4 ; ° E ; E Q The most stable conformers of the furanose ring are the envelope and twist forms; these can exist in 10 arrangements each.

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. (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.

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