Oligoaminudeoside phosphoramidates. Oligomeilzation of dimers of 3′-amino-3′-deoxy-nucleotides (GC and CG) in aqueous solution
Open accessAbstract
The self-complementary 5'-phosphorylated dinucleoside 3' (N)----5' (P)-linked phosphoramidates with sequence GC (8a), CG (8b) and the tetranucleoside triphosphoramidate with sequence GCGC (10a) and CGCG (10b) have been synthesized and characterized by physicochemical and enzymatic methods. The dinucleosides 8a or 8b oligomerize in aqueous solution in the presence of a water-soluble carbodiimide. This process is efficient and regiospecific. In the case of GC it produces alternating 3' (N)----5' (P)-linked phosphoramidates up to 15 dimeric units in length with a yield in excess of 70%. The oligomerization of the CG isomer is much less efficient. The mechanism of oligomerization is discussed.
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- Authors
- Zielinski, W. S., & Orgel, L. E.
- Affiliations
- Salk Institute for Biological Studies (US)
- Venue
- Nucleic Acids Research
- Publisher
- Oxford University Press (OUP)
- Published
- 1987
- Volume
- 15
- Issue
- 4
- Pages
- 1699-1715
- ISSN
- 0305-1048 (ISSN-L)
- 1362-4962
- PMC
- PMC340575
- OpenAlex
- W2035569593
- Cited by
- 49
- References
- 7
- Citations by year
- 2024: 1 · 2022: 1 · 2020: 1 · 2019: 2 · 2018: 1 · 2015: 3 · 2014: 1 · 2012: 1
- FWCI
- 0.83
- Type
- journal article
- Language
- en
- Open access
- green
- europepmc.org
- Locations
- Nucleic Acids Research (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Physical Sciences › Chemistry › Organic Chemistry › Organophosphorus compounds synthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Advanced biosensing and bioanalysis techniques
- Keywords
- oligomerization, CG dinucleotides, carbodiimides, oligonucleotide synthesis, oligomerization mechanism
- MeSH terms
- Base Sequence, Chromatography, High Pressure Liquid, Cytosine, Guanine, Indicators and Reagents, Kinetics, Oligodeoxyribonucleotides, Solutions
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