An Efficient Method for the Synthesis of [4–15N]Cytidine, 2′-Deoxy[4–15N]Cytidine, [6–15N]adenosine, and 2′-Deoxy [6–15N]adenosine Derivatives # 1

Abstract Nucleophilic substitution reactions of 4-azolyl-1 β-P-D-ribofuranosylpyrimidin-2(1H)-one and 6-azolyl-9-β-D-ribofuranosyl-9H-purine derivatives, which were converted from uridine and inosine, with [15N]phthalimide in the presence of triethylamine or DBU gave N 4-phthaloyl[4-15N]cytidine and N 6-phthaloyl[6-15N]- adenosine derivatives, respectively, in high yields. Similar reactions of those azolyl derivatives with succinimide afforded N 4-succinylcytidine and N 6-succinyladenosine derivatives in high yields. The corresponding 2′-deoxyribonucleosides were also synthesized efficiently through the same procedure. 1. Partial Protection of Carbohydrate Derivatives. Part 31. For Part 30, see Aoyama, Y.; Sekine, T.; Iwamoto, Y.; Kawashima, E.; Ishido, Y. Nucleosides Nucleotides, submitted. The present work has partly been communicated (cf. Kamaike, K.; Takahashi, M.; Utsugi, K.; Tomizuka, K.;Ishido, Y. Tetrahedron Lett. 1995, 36, 91–94.). #This paper is dedicated to Dr. Yoshihisa Mizuno on the occasion ...

[1]  Mihoko Takahashi,et al.  An efficient method for the synthesis of [4-15N]cytidine and [6-15N]adenosine derivatives from uridine and inosine , 1995 .

[2]  M. Sako,et al.  A Newly Devised Method for the Debenzylation of N 6-Benzyladenosines. A Convenient Synthesis of [6-15 N]-Labeled Adenosines , 1994 .

[3]  E. Pedersen,et al.  A convenient method for the synthesis of L-3'-amino-2',3'-dideoxyuridines , 1989 .

[4]  A. Bax,et al.  NMR signal assignments of amide protons in the alpha-helical domains of staphylococcal nuclease. , 1988, Biochemistry.

[5]  Y. Ishido,et al.  A Simple, Preparative Procedure for N 3-Anisoyluridine and O 6-Diphenylcarbamoylguanosine 2′-O-(Tetrahydropyran-2-YL) Derivatives via The Corresponding 3′,5′-Dibenzoates , 1988 .

[6]  V. Kansal,et al.  Synthesis of 6-15N and 1-15N labeled adenosine monophosphates , 1988 .

[7]  Y. Ishido,et al.  Partial Protection of Carbohydrate Derivatives. Part 23.1 Simple, Efficient Procedure for the Preparation of 3′- and 2′-0-(Tetrahydropyran-2-YL)Ribonucleoside Derivatives Involving Highly Regioselective 2′,5′-DI-O-Acylation or that Followed by Acyl Migration on Silica Gel and Subsequent O-(Tetrahydr , 1987 .

[8]  J. Schmidt,et al.  15N labeling of oligodeoxynucleotides for NMR studies of DNA-ligand interactions. , 1987, Nucleic acids research.

[9]  R. Griffey,et al.  Proton NMR measurements of bacteriophage T4 lysozyme aided by 15N isotopic labeling: structural and dynamic studies of larger proteins. , 1987, Proceedings of the National Academy of Sciences of the United States of America.

[10]  Roger A. Jones,et al.  Nitrogen-15 labeled deoxynucleosides. Synthesis of 15N6-and 15N1-deoxyadenosines from deoxyadenosine , 1987 .

[11]  K Wüthrich,et al.  NMR studies of the complex between the decadeoxynucleotide d-(GCATTAATGC)2 and a minor-groove-binding drug. , 1986, Biochemistry.

[12]  W. Brill,et al.  NMR studies of DNA recognition sequences and their interaction with proteins. The phage lambda OR1 operator, a symmetric lac operator and their specific complexes with cro protein and lac repressor "headpiece". , 1986, Journal of biomolecular structure & dynamics.

[13]  A. Gronenborn,et al.  Conformation of the DNA undecamer 5'd(A-A-G-T-G-T-G-A-T-A-T) bound to the single-stranded DNA binding protein of Escherichia coli. A time-dependent transferred nuclear Overhauser enhancement study. , 1986, Journal of molecular biology.

[14]  R. Adamiak,et al.  New, ionic side-products in oligonucleotide synthesis: formation and reactivity of fluorescent N-/purin-6-yl/pyridinium salts. , 1985, Nucleic acids research.

[15]  M. Sekine,et al.  Cyclic diacyl groups for protection of the N6-amino group of deoxyadenosine in oligodeoxynucleotide synthesis. , 1984, Nucleic acids research.

[16]  C. Niu.  Synthesis of [4-15NH2]- and [1,3-15N2]cytidine derivatives for use in NMR-monitored binding tests. , 1984, Analytical biochemistry.

[17]  H. Rüterjans,et al.  1H NMR study of the interaction of bacteriophage lambda Cro protein with the OR3 operator. Evidence for a change of the conformation of the OR3 operator on binding. , 1984, Nucleic acids research.

[18]  M. Sekine,et al.  Phthaloyl group : a new amino protecting group of deoxyadenosine in oligonucleotide synthesis , 1982 .

[19]  K. Okazaki,et al.  Partial protection of carbohydrate derivatives. Part 4. Regioselective 2′-O-deacylation of fully acylated purine and pyrimidine ribonucleosides with hydroxylaminium acetate , 1979 .

[20]  C. Poulter,et al.  [3-15N]-2′,3′,5′-tri-o-benzoyluridine. Detection of hydrogen bonding in a-u base pairs by 15N NMR.☆ , 1979 .

[21]  H. Schmidt,et al.  Notiz zum Mechanismus der Dimroth‐Umlagerung am Adeninring , 1977 .

[22]  J. McCloskey,et al.  Isotopic labeling studies of the base-catalyzed conversion of 1-methyladenosine to N 6 -methyladenosine. , 1973, The Journal of organic chemistry.

[23]  B. Griffin,et al.  The synthesis of oligoribonucleotides. IV. Preparation of dinucleoside phosphates from 2',5'-protected ribonucleoside derivatives. , 1968, Tetrahedron.

[24]  S. Varadarajan,et al.  462. Nucleotides. Part XXXVII. The structure of uridylic acids a and b, and a synthesis of spongouridine (3-β-D-arabofuranosyluracil) , 1956 .

[25]  H. Bredereck.  Über methylierte Nucleoside und Purine und ihre pharmakologischen Wirkungen, I. Mitteil.: Methylierung von Nucleosiden durch Diazomethan , 1947 .