Home LiteratureArticle Details
PMID: 2829119 Published · ppublish English Journal Article

DNA containing the base analogue 2-aminoadenine: preparation, use as hybridization probes and cleavage by restriction endonucleases.

Nucleic acids research ·Vol. 16 ·No. 1 ·1988-01-11 ·Pages 305-17

Chollet A, Kawashima E

Abstract

The base analogue 2-aminoadenine (2,6-diaminopurine, D) has been introduced at selected positions into synthetic oligodeoxyribonucleotides and DNA by the combined use of chemical and enzymatic methods. 2-aminoadenine substitution for adenine introduces changes in the minor groove of DNA and creates an additional hydrogen bond in the Watson-Crick base pair with thymine. Oligonucleotide hybridization probes containing 2-aminoadenine showed increased selectivity and hybridization strength during DNA-DNA hybridization to phage or genomic target DNA. Properties of the base analogue with respect to DNA modifying enzymes were examined. 2-aminoadenine was used to probe minor groove determinants during the treatment of DNA by 12 restriction endonucleases. Inhibition of cleavage was found for several restriction enzymes.

MeSH Terms
2-Aminopurine/analogs & derivatives Adenine/analogs & derivatives Base Sequence DNA/chemical synthesis DNA Restriction Enzymes Indicators and Reagents Molecular Sequence Data Nucleic Acid Hybridization Oligodeoxyribonucleotides/chemical synthesis Templates, Genetic
Chemicals
Indicators and Reagents Oligodeoxyribonucleotides 2-Aminopurine 2,6-diaminopurine DNA DNA Restriction Enzymes Adenine
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Chollet A
Department of Chemistry, Biogen SA, Geneva, Switzerland.
Kawashima E
References (37)
37 references, click to expand
  1. Studies on polynucleotides. 118. A further study of ribonucleotide incorporation into deoxyribonucleic acid chains by deoxyribonucleic acid polymerase I of Escherichia coli.
    J Biol Chem. 1972 Oct 10;247(19):6140-8 PMID: 4568603
  2. THE MUTAGENIC ACTIVITY OF 2-AMINOPURINE AND 2,6-DIAMINOPURINE ON PHAGE T4 GROWN ON NON-INHIBITED AND CHLORAMPHENICOL-INHIBITED CELLS OF ESCHERICHIA COLI B.
    Mutat Res. 1964 Jul;106:205-8 PMID: 14237072
  3. Detection of specific sequences among DNA fragments separated by gel electrophoresis.
    J Mol Biol. 1975 Nov 5;98(3):503-17 PMID: 1195397
  4. EcoRI methylase. Physical and catalytic properties of the homogeneous enzyme.
    J Biol Chem. 1977 Oct 25;252(20):7265-72 PMID: 332688
  5. Role of the 2-amino group of deoxyguanosine in sequence recognition by EcoRI restriction and modification enzymes.
    J Biol Chem. 1977 Oct 25;252(20):7273-8 PMID: 332689
  6. 2-aminoadenine is an adenine substituting for a base in S-2L cyanophage DNA.
    Nature. 1977 Nov 24;270(5635):369-70 PMID: 413053
  7. How lac repressor recognizes lac operator.
    Proc Natl Acad Sci U S A. 1978 Aug;75(8):3578-82 PMID: 278973
  8. Digestion of 5-bromodeoxyuridine-substituted lambda-DNA by restriction endonucleases.
    J Biol Chem. 1978 Dec 25;253(24):9075-81 PMID: 721831
  9. The effects of substituted pyrimidines in DNAs on cleavage by sequence-specific endonucleases.
    J Biol Chem. 1979 Apr 10;254(7):2551-60 PMID: 372183
  10. [Molecular mechanisms of 2-aminopurine and 2,6-diaminopurine induced mutations].
    Mol Biol (Mosk). 1979 Jul-Aug;13(4):822-8 PMID: 470939
  11. Hybridization of synthetic oligodeoxyribonucleotides to phi chi 174 DNA: the effect of single base pair mismatch.
    Nucleic Acids Res. 1979 Aug 10;6(11):3543-57 PMID: 158748
  12. Deoxyribonucleotide pools, base pairing, and sequence configuration affecting bromodeoxyuridine- and 2-aminopurine-induced mutagenesis.
    Proc Natl Acad Sci U S A. 1980 Apr;77(4):1801-5 PMID: 6929522
  13. Single-strand and double-strand cleavage at half-modified and fully modified recognition sites for the restriction nucleases Sau3a and Taqi.
    Gene. 1980 Dec;12(3-4):267-75 PMID: 6265320
  14. Use of synthetic oligonucleotides as hybridization probes: isolation of cloned cDNA sequences for human beta 2-microglobulin.
    Proc Natl Acad Sci U S A. 1981 Nov;78(11):6613-7 PMID: 6171820
  15. Digestion of highly modified bacteriophage DNA by restriction endonucleases.
    Nucleic Acids Res. 1982 Mar 11;10(5):1579-91 PMID: 6280151
  16. Ordered water structure around a B-DNA dodecamer. A quantitative study.
    J Mol Biol. 1983 Jan 5;163(1):129-46 PMID: 6834428
  17. An efficient method for the sequence analysis of oligodeoxyribonucleotides.
    Anal Biochem. 1983 Feb 1;128(2):281-6 PMID: 6846805
  18. Effect of nucleotide analogs on the cleavage of DNA by the restriction enzymes AluI, DdeI, HinfI, RsaI, and TaqI.
    J Biol Chem. 1983 Dec 25;258(24):15206-13 PMID: 6317689
  19. Genomic sequencing.
    Proc Natl Acad Sci U S A. 1984 Apr;81(7):1991-5 PMID: 6326095
  20. The B----Z transition in two synthetic oligonucleotides: d(C-2-amino-ACGTG) and d(m5CGCAm5CGTGCG) studied by IR, NMR and CD spectroscopies.
    Nucleic Acids Res. 1984 Aug 10;12(15):6291-305 PMID: 6332307
  21. Base composition-independent hybridization in tetramethylammonium chloride: a method for oligonucleotide screening of highly complex gene libraries.
    Proc Natl Acad Sci U S A. 1985 Mar;82(6):1585-8 PMID: 3856838
  22. Solid-phase synthesis of the self-complementary hexamer d(c7GpCpc7GpCpc7GpC) via the O-3'-phosphoramidite of 7-deaza-2'-deoxyguanosine.
    Nucleic Acids Res. 1985 Feb 11;13(3):911-26 PMID: 4000931
  23. Biotin-labeled synthetic oligodeoxyribonucleotides: chemical synthesis and uses as hybridization probes.
    Nucleic Acids Res. 1985 Mar 11;13(5):1529-41 PMID: 4000941
  24. Elucidation of the mechanism of selective inhibition of mammalian DNA polymerase alpha by 2-butylanilinopurines: development and characterization of 2-(p-n-butylanilino)adenine and its deoxyribonucleotides.
    Nucleic Acids Res. 1985 Sep 11;13(17):6331-42 PMID: 3931053
  25. Molecular cloning and expression of human tumor necrosis factor and comparison with mouse tumor necrosis factor.
    Eur J Biochem. 1985 Nov 4;152(3):515-22 PMID: 3932069
  26. T4 RNA ligase catalyzed synthesis of base analogue-containing oligodeoxyribonucleotides and a characterization of their thermal stabilities.
    Nucleic Acids Res. 1985 Dec 20;13(24):8665-84 PMID: 4080551
  27. Poly(d2NH2A-dT): two-dimensional NMR shows a B to A conversion in high salt.
    Biochemistry. 1985 Dec 3;24(25):7456-62 PMID: 4084592
  28. The effects of base analogue substitutions on the cleavage by the EcoRI restriction endonuclease of octadeoxyribonucleotides containing modified EcoRI recognition sequences.
    J Biol Chem. 1986 Jun 5;261(16):7270-8 PMID: 3011780
  29. The effects of base analogue substitutions on the methylation by the EcoRI modification methylase of octadeoxyribonucleotides containing modified EcoRI recognition sequences.
    J Biol Chem. 1986 Jun 5;261(16):7279-86 PMID: 3011781
  30. Synthesis and properties of defined DNA oligomers containing base mispairs involving 2-aminopurine.
    Nucleic Acids Res. 1986 Jul 25;14(14):5869-84 PMID: 3737416
  31. Oligonucleotide duplexes containing inosine, 7-deazainosine, tubercidin, nebularine and 7-deazanebularine as substrates for restriction endonucleases HindII, SalI and TaqI.
    Nucleic Acids Res. 1986 Aug 26;14(16):6579-90 PMID: 3018674
  32. Studies on nucleic acid interactions. I. Stabilities of mini-duplexes (dG2A4XA4G2-dC2T4YT4C2) and self-complementary d(GGGAAXYTTCCC) containing deoxyinosine and other mismatched bases.
    Nucleic Acids Res. 1986 Oct 10;14(19):7727-36 PMID: 3774544
  33. Synthesis and properties of oligonucleotides containing 2'-deoxynebularine and 2'-deoxyxanthosine.
    Nucleic Acids Res. 1986 Oct 24;14(20):8135-53 PMID: 3095793
  34. Structure of the DNA-Eco RI endonuclease recognition complex at 3 A resolution.
    Science. 1986 Dec 19;234(4783):1526-41 PMID: 3024321
  35. Minor-groove-modified oligonucleotides: synthesis of decadeoxynucleotides containing hypoxanthine, N2-methylguanine and 3-deazaadenine, and their interactions with restriction endonucleases Bgl II, Sau, 3AI, and Mbo I (Nucleosides and Nucleotides Part 75).
    Nucleic Acids Res. 1987 Apr 10;15(7):3059-72 PMID: 3031618
  36. Crystal structure of a Z-DNA fragment containing thymine/2-aminoadenine base pairs.
    J Biomol Struct Dyn. 1986 Oct;4(2):157-72 PMID: 3271437
  37. Chain length determination of small double- and single-stranded DNA molecules by polyacrylamide gel electrophoresis.
    Biochemistry. 1975 Aug 26;14(17):3787-94 PMID: 1174504
Article Info
Journal
Nucleic acids research
Abbr.
Nucleic Acids Res
ISSN
0305-1048
Published
1988-01-11
Pages
305-17
Language
English
Region
England
NLM ID
0411011
PMCID
PMC334628
Subset
IM
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: [email protected]