Kiyofumi Fukukawa

A facile one-step synthesis of 5′-phosphatidylnucleosides by an enzymatic two-phase reaction.

Abstract Phospholipase D from Streptomyces effectively catalyzed the transfer reaction of the phosphatidyl residue from phosphatidylcholines to the 5′-hydroxyl group of nucleosides in a two-phase system. A variety of 5′-phosphatidylnucleosides were easily prepared in high yields by this reaction.

Enantioselective synthesis of new analogs of neplanocin A and their biological activity

Abstract Various carbocyclic nucleosides analogs of neplanocin A (such as 5-aminoimidazole-4-carboxamide riboside, uridine, 5-iodouridine, 4-thiouridine, cytidine, thymidine, 2′-deoxyguanosine, ribofuranosylthymine, a 2,2′-anhydroderivative, 2′-deoxycytidine, 2′-deoxythiouridine, and d -arabinofuranosylcytosine analogs) were synthesized from (1 R , 2 S , 3 R )-2,3-isopropylidenedioxy-4-methoxymethyloxymethyl-4-cyclopentenylamine. The cytidine analog was found the most active in inhibiting mouse lymphoma L5178Y cells in vitro at a concentration as low as 0.8 μg/mL.

The Structure of 2′ (R)-Mercapto-2′-deoxyneplanocin A (Nucleosides and Nucleotides 48.)

Abstract The molecular and crystal structure of 2′(R)-mercapto-2′-deoxyneplanocin A, C11H13N5O2S M.W.=279.32, has been determined by X-ray analysis. The space group is P212121 with a=10.322(1), b=22.870(2), c=5.273(1)A and z=4. The structure was solved by direct method, and least-squares refinement using 1806 reflections with |Fo| > 30(F) led to the final R value of 0.045. The sugar C(2′) atom is displaced by 0.35A opposite to the base N(9), i.e., C(2′)-exo conformation and the torsion angle about the N(9)-C(1) bond is 26.3(4)° (anti conformation).