Efficient chemo-enzymatic syntheses of pharmaceutically useful unnatural 2′-deoxynucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 24, Issue 5-7, 2005, Pages 1127-1130

  Komatsu, Hironori ^a   Araki, Tadashi ^a  

^a MITSUI CHEMICALS INC   (Japan)

Author keywords

2 Chloro 2 Deoxyadenosine; 2 Deoxy D Ribose 1 Phosphate; Cladribine; dRP; Glycosylation; Purine Nucleoside Phosphorylase

Indexed keywords

2 DEOXYRIBOSE 1 PHOSPHATE; 2' DEOXYNUCLEOSIDE; 9 (2 DEOXY BETA DEXTRO 1 RIBOSYL) 2,6 DICHLOROPURINE; CLADRIBINE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; CRYSTALLIZATION; DRUG SYNTHESIS; GLYCOSYLATION; NUCLEOTIDE METABOLISM; STEREOCHEMISTRY;

ANTINEOPLASTIC AGENTS; CLADRIBINE; GLYCOSYLATION; MODELS, CHEMICAL; NUCLEOSIDES; NUCLEOTIDES; PHOSPHATES; PURINE-NUCLEOSIDE PHOSPHORYLASE;

EID: 26644461700     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1081/NCN-200060154     Document Type: Conference Paper

References (8)

1. Komatsu, H.; Awano, H.; Tanikawa, H.; Itou, K.; Ikeda, I. Large-scale manufacturing of all four 2′-deoxynucleosides via novel strategies including a chemo-enzymatic process. Nucleosides Nucleotides Nucleic Acids 2001, 20, 1291.
2. Komatsu, H.; Awano, H.; Ishibashi, H.; Oikawa, T.; Ikeda, I.; Araki, T. Chemo-enzymatic syntheses of natural and unnatural 2′-deoxynucleosides. Nucleic Acids Res. Suppl. 2003, 3, 101.
3. Komatsu, H.; Awano, H. First stereoselective synthesis of 2-deoxy-alpha-D-ribosyl-1-phosphate: novel application of crystallization- induced asymmetric transformation. J. Org. Chem. 2002, 67, 5419.
4. Komatsu, H.; Araki, T. Chemo-enzymatic synthesis of 2′,3′- dideoxy-3′-fluoro-β-D-guanosine via 2,3-dideoxy-3-fluoro-α-D- ribose 1-phosphate. Tetrahedron Lett. 2003, 44, 2899.
5. Janeba, Z.; Francom, P.; Robins, M.J. Efficient syntheses of 2-chloro-2′-deoxyadenosine (cladribine) from 2′-deoxyguanosine(1). J. Org. Chem. 2003, 68, 989, and references therein.
6. Brown, G.B.; Weliky, V.S. 2-Chloroadenine and 2-chloroadenosine. J. Org. Chem. 1958, 23, 125.
7. Jensen, K.F.; Nygaard, P. Purine nucleoside phosphorylase from Escherichia coli and Salmonella typhimurium. Purification and some properties. Eur. J. Biochem. 1975, 51, 253.
8. Krenitsky, T.A.; Koszalka, G.W.; Tuttle, J.V. Purine nucleoside synthesis, an efficient method employing nucleoside phosphorylases. Biochemistry 1981, 20, 3615.