Synthesis of 2-deoxy-beta-D-ribose 1-phosphate, NMR comparison and its enzymatic activity for structural elucidation of synthetic alpha-isomer.
2-Deoxy-beta-D-ribose 1-phosphate (1) was synthesized in a stereoselective manner and isolated with no detectable contamination by its alpha-isomer (4). Explicit configuration of 4 was first determined by NMR comparison with 1 judging from NOE results and their coupling constants. Natural purine nucleoside phosphorylase (PNPase) did not recognize 1 and gave no products such as alpha- or beta-deoxynucleosides.
Komatsu
Hironori
H
Catalysis Science Laboratory, Mitsui Chemicals Inc., Sodegaura-shi, Chiba, Japan. hironori.komatsu@mitsui-chem.co.jp
Ikeda
Ichirou
I
D003853:Deoxyribonucleosides / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011683:Purine-Nucleoside Phosphorylase / Q000378:metabolism*; D012267:Ribosemonophosphates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
D003853:Deoxyribonucleosides; D012267:Ribosemonophosphates; C031302:2-deoxyribose 1-phosphate; D011683:Purine-Nucleoside Phosphorylase