Chiroptical studies of 1-thio-D-glycofuranosides, an interpretation of hudson's isorotation rule.

✍ Scribed by Hiroshi Meguro; Emiri Ohtaki; Katura Tuzimura

• Book ID: 104235798
• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 237 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83501-2

✦ Synopsis

Hudson's isorotation rule has been used for the determination of the 1) anomeric configuration of sugars. Fundamentally sugars have functional groups of two types -OH and -O-C-O-. In spite of the recent progress of circular dichroism (CD) and optical rotatory dispersion (ORD) studiegT5)the rule remains still empirical , partly because of the lack of the Cotton effect in the measurable wavelength region together with the difficulty in differentiating several bands at similar wavelengths. In the UV the hydroxyl (-OH) and alkoxyl (-OR) groups have the first band at 180-195 nm and the second band at 140-175 nm in the vacuum ultraviolet regio 8!7) The replacement of the oxygen by a sulfur atom is known to cause a red shift of about 30-40 nm. Thus thioalkyl (-SR) and thiol (-SH) groups gave the corresponding first and second band at 220-250 nrn and 180-200 nm8) e On the hypothetical basis of the resemblance of sulfur and oxygen here we report ORD and CD of I-thio-g-glycofuranosides (I)-(V) in Fig.1 as model compounds of glycofuranosides taking advantage of the above red shift.