Description
An N-substituted putrescine that is thymine in which a hydrogen of the methyl group has been replaced by one of the amino groups of putrescine. It replaces about half of the thymine residues in the DNA of bacetriophage phiW-14.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C9H16N4O2 | 0 | 212.249 |
Recommended notation
| Name | α-putrescinylthymine |
|---|---|
| Abbreviation | putThy |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 5-{[(4-aminobutyl)amino]methyl}pyrimidine-2,4(1H,3H)-dione | N1C=C(C(NC1=O)=O)CNCCCCN | InChI=1S/C9H16N4O2/c10-3-1-2-4-11-5-7-6-12-9(15)13-8(7)14/h6,11H,1-5,10H2,(H2,12,13,14,15) | IBOLVNKLOOYDDG-UHFFFAOYSA-N |
|
Nature
| Origin | Function | Functional detail |
Organisms
|
References |
|---|---|---|---|---|
| natural | hypermodified nucleobase | bacteriophage ϕW-14 |
|
Citations
- Gerhard, B, et al. 1982. Reactivity of the alpha-putrescinylthymine amino groups in phi W-14 deoxyribonucleic acid. Biochemistry. 21(22).
- Kelln, RA, et al. 1973. Studies on the biosynthesis of alpha-putrescinylthymine in bacteriophage phi W-14-infected Pseudomonas acidovorans. Journal of Virology. 12(6).
- Kropinski, AM, et al. 1973. 5-(4-Aminobutylaminomethyl)uracil, an unusual pyrimidine from the deoxyribonucleic acid of bacteriophage phiW-14. Biochemistry. 12(1).
- Kropinski, AM, et al. 1983. alpha-Putrescinylthymine. Methods in Enzymology. 94.
- Maltman, KL, et al. 1980. Synthesis of thymine and alpha-putrescinylthymine in bacteriophage phi W-14-infected Pseudomonas acidovorans. Journal of Virology. 34(2).
- Maltman, KL, et al. 1981. 5-[(Hydroxymethyl)-O-pyrophosphoryl]uracil, an intermediate in the biosynthesis of alpha-putrescinylthymine in deoxyribonucleic acid of bacteriophage phi W-14. Biochemistry. 20(12).
- Miller, PB, et al. 1985. alpha-Putrescinylthymine and the sensitivity of bacteriophage phi W-14 DNA to restriction endonucleases. Nucleic Acids Research. 13(7).
- Miller, PB, et al. 1983. Formation and possible functions of alpha-putrescinylthymine in bacteriophage phi W-14 DNA: analysis of bacteriophage mutants with decreased levels of alpha-putrescinylthymine in their DNAs. Journal of Virology. 47(3).
- Takeda, T, et al. 1983. Synthesis of oligonucleotides containing the hypermodified base, alpha-putrescinylthymine. Nucleic Acids Symposium Series. (12).