The mutarotation of 2-deoxy-β-d-erythro-pentose (“2-deoxy-β-d-ribose”)
1971; Elsevier BV; Volume: 20; Issue: 1 Linguagem: Inglês
10.1016/s0008-6215(00)84949-6
ISSN1873-426X
AutoresR. U. Lemieux, Laurens Anderson, Anthony H. Conner,
Tópico(s)Biochemical Analysis and Sensing Techniques
ResumoIn aqueous solution, 2-deoxy-β-d-erythro-pentopyranose retains the 1C conformation of the solid. On mutarotation in water, the sugar rearranges, to give an equilibrium mixture containing the β-d-pyranose, α-d-pyranose (1C conformation), β-d-furanose, and α-d-furanose forms in the approximate ratios of 43:42:10:5 at 0° and 15:15:9:11 at 90°. The mutarotation is kinetically "complex", with a rate constant for the approach of the furanoses to their equilibrium level substantially greater than the constants for the pyranoses. The results, based on p.m.r. and optical rotatory measurements, are discussed in terms of conformational and isomer predisposition.
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