Nucleic acid related compounds. 6. Sugar-modified N6-(3-methyl-2-butenyl)adenosine derivatives, N6-benzyl analogs, and cytokinin-related nucleosides containing sulfur or formycin

Biochemistry ◽  
1973 ◽  
Vol 12 (12) ◽  
pp. 2179-2187 ◽  
Author(s):  
Morris J. Robins ◽  
E. M. Trip
Keyword(s):  
Nucleic Acid ◽  
Adenosine Derivatives ◽  
Related Compounds

Nucleic acid related compounds. 77. 2′,3′-Didehydro-2′,3′-dideoxy-2′(and 3′)-methylnucleosides via [3,3]-sigmatropic rearrangements of 2′(and 3′)-methylene-3′(and 2′)-O-thiocarbonyl derivatives and radical reduction of a 2′-chloro-3′-methylene analogue

1993 ◽  
Vol 71 (2) ◽  
pp. 186-191 ◽  
Author(s):  
Vincente Samano ◽  
Morris J. Robins
Keyword(s):  
Nucleic Acid ◽  
Sigmatropic Rearrangement ◽  
Sigmatropic Rearrangements ◽  
Radical Reduction ◽  
Adenosine Derivatives ◽  
Related Compounds

Treatment of 5′-O-(tert-butyldiphenylsilyl)-2′(and 3′)-deoxy-2′(and 3′)-methyleneuridine (and adenosine) derivatives with phenyl chlorothionocarbonate gave the 3′(and 2′)-O-phenoxythiocarbonyl intermediates, which underwent spontaneous [3,3]-sigmatropic rearrangement to give the 2′,3′-didehydro-2′,3′-dideoxy-2′(and 3′)-(phenoxycarbonylthio)methyl analogues. These allylic thioesters were subjected to tributylstannane-mediated hydrodesulfurization and deprotection to give 2′,3′-didehydro-2′,3′-dideoxy-2′(and 3′)-methyluridine (and adenosine). Tributylstannane-mediated hydrodehalogenation of a 2′-chloro-2′,3′-dideoxy-3′-methyleneuridine derivative afforded the 2′,3′-didehydro-2′,3′-dideoxy-3′-methyl product of allylic transposition exclusively.

scholarly journals THE ASSIMILATION OF NUCLEIC ACID DERIVATIVES AND RELATED COMPOUNDS BY YEASTS

1951 ◽  
Vol 189 (1) ◽  
pp. 151-157 ◽  
Author(s):  
Frederick J. Di Carlo ◽  
Alfred S. Schultz ◽  
Doris K. McManus
Keyword(s):  
Nucleic Acid ◽  
Related Compounds

Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides

1983 ◽  
Vol 26 (5) ◽  
pp. 661-666 ◽  
Author(s):  
Erik De Clercq ◽  
Johan Descamps ◽  
Jan Balzarini ◽  
Jerzy Giziewicz ◽  
Philip J. Barr ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Biological Activities ◽  
Related Compounds

Nucleic Acid Related Compounds. 5. The Transformation of Formycin and Tubercidin into 2′- and 3′-Deoxynucleosides

1973 ◽  
Vol 51 (9) ◽  
pp. 1313-1321 ◽  
Author(s):  
Morris J. Robins ◽  
James R. McCarthy Jr. ◽  
Roger A. Jones ◽  
Rudolf Mengel
Keyword(s):  
Nucleic Acid ◽  
Mass Spectra ◽  
Sodium Iodide ◽  
Excess Sodium ◽  
Related Compounds

Reaction of tubercidin (4-amino-7-β-D-ribofuranosylpyrrolo[2,3-d]pyrimidine) (1) with α-acetoxyisobutyryl chloride in the presence of excess sodium iodide in acetonitrile gave an acylated iodo intermediate (2) which was converted into 3′-deoxytubercidin (4) by hydrogenolysis and subsequent saponification.Analogous treatment of formycin (7-amino-3-β-D-ribofuranosylpyrazolo[4,3-d]pyrimidine) (5) gave 3′-deoxyformycin (6) and 2′-deoxyformycin (7) in an approximate ratio of 3:2. These purified nucleosides, 6 and 7 were individually deaminated enzymatically to give 3′-deoxyformycin B (8) and 2′-deoxyformycin B(9).Biological rationale, n.m.r., and mass spectra of these antibiotic-derived deoxynucleosides are discussed.

Nucleic acid related compounds. 63. Synthesis of 5′-deoxy-5′-methyleneadenosine and related Wittig-extended nucleosides

1991 ◽  
Vol 69 (2) ◽  
pp. 334-338 ◽  
Author(s):  
Stanislaw F. Wnuk ◽  
Morris J. Robins
Keyword(s):  
Nucleic Acid ◽  
Key Words ◽  
Organic Bases ◽  
Key Words Adenosine ◽  
Tosyl Group ◽  
High Yields ◽  
Related Compounds

Treatment of the purified 5′-aldehyde (2a) (derived from 6-N-benzoyl-2′,3′-O-isopropylideneadenosine (1a)) with methylenetriphenylphosphorane and successive deprotection with ammonia and acid gave 9-(5,6-dideoxy-β-D-ribo-hex-5-enofuranosyl)adenine (5′-deoxy-5′-methyleneadenosine) (4). Oxidation of 1a or 2′,3′-O-isopropylideneadenosine (1b) and treatment of the crude 5′-aldehydes (2a or 2b) with (p-toluenesulfonylmethylene)triphenylphosphorane gave high yields of the 5′-deoxy-5′-tosylmethylene derivatives (5a or 5b). Removal of the tosyl group from 5b to give 3b was effected with tributylstannyllithium, but sulfone cleavage by the usual reductive methods failed. Reduction and deprotection of 5a or 5b gave 9-[5,6-dideoxy-6-(p-toluenesulfonyl)-β-D-ribo-hexofuranosyl]adenine (6b). Isomerization of the vinyl tosyl (5b) to a 4′,5′-unsaturated allylic tosyl derivative (7) occurred under cleavage conditions and in solutions of aqueous or organic bases. Key words: adenosine, 5′-deoxyadenosine, 5′-methylene-5′-deoxyadenosine, nucleosides.

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