(S)-1-(2,3-Dihydroxypropyl)cytosine
4-amino-1-[(2S)-2,3-dihydroxypropyl]pyrimidin-2-one
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- Nom chimique
- 4-amino-1-[(2S)-2,3-dihydroxypropyl]pyrimidin-2-one
- FM
- C7H11N3O3
- PM
- 185.18
- Pureté
- >=98%
(S)-1-(2,3-Dihydroxypropyl)cytosine is the unprotected (S)-GNA (glycol nucleic acid) cytosine nucleoside: a cytosine joined at N1 to an acyclic (S)-2,3-dihydroxypropyl "glycol" backbone in place of a ribose or deoxyribose sugar. CHEMOS lists it as catalog CH70002 with CAS 55559-70-1, molecular formula C7H11N3O3, and molecular weight 185.18 (PubChem CID 11805434; InChIKey LTTDCEYZEHQDGW-YFKPBYRVSA-N).
This is the parent glycol-cytosine unit: protecting the base and differentiating the two backbone hydroxyls yields the (S)-GNA-C phosphoramidite used to add a GNA cytosine during solid-phase oligonucleotide synthesis. According to PubMed, glycol nucleic acid is an acyclic nucleic-acid analog joined by phosphodiester bonds that is incorporated into oligonucleotides via phosphoramidite chemistry, and an (S)-GNA nucleotide increases resistance to nuclease degradation while having little impact on duplex structure.
Synonymes
(S)-GNA-C; 1-[(S)-2,3-dihydroxypropyl]cytosine; (S)-glycol cytosine nucleoside
Identité et spécifications
| Catalog No. | CH70002 |
| CAS No. | 55559-70-1 |
| Molecular Formula | C7H11N3O3 |
| Molecular Weight | 185.18 |
| PubChem CID | 11805434 |
| InChIKey | LTTDCEYZEHQDGW-YFKPBYRVSA-N |
| Backbone | (S)-GNA (glycol nucleic acid), unprotected cytosine |
| Purity | >=98% |
Caractéristiques techniques
- Material class
- (S)-GNA nucleoside
- Nucleobase
- Cytosine
- Backbone scaffold
- (S)-2,3-dihydroxypropyl
- Protection state
- Unprotected
- Packaging
- 10 mg; 25 mg; 50 mg; 100 mg; Custom packaging on request
Contexte d’application
- Parent (S)-GNA-C nucleoside: the plain glycol-cytosine unit from which the base-protected monomer and (S)-GNA-C phosphoramidite are prepared.
- Acyclic backbone unit: the (S)-2,3-dihydroxypropyl glycol replaces the sugar ring, the defining feature of a GNA nucleotide.
- Nuclease-resistance research: according to PubMed, (S)-GNA incorporation has been studied for increasing resistance to exonuclease/phosphodiesterase degradation in siRNA duplexes.
Ressources techniques associées
Sources publiques
- Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing
Journal of Organic Chemistry, 2021
Product-family technical context
- Solid-phase supports for oligonucleotide synthesis
Current Protocols in Nucleic Acid Chemistry, 2013
Product-family technical context
- Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis
Tetrahedron Letters, 1981
Product-family technical context
- Synthesis of deoxyoligonucleotides on a polymer support
Journal of the American Chemical Society, 1981
Product-family technical context
- Composé PubChem 11805434
PubChem · CID 11805434
Questions fréquentes
How does an (S)-GNA cytosine differ from a normal cytidine?
In place of the ribose/deoxyribose sugar ring, the cytosine sits on an acyclic (S)-2,3-dihydroxypropyl (glycol) backbone. This is the defining feature of glycol nucleic acid (GNA), a simplified acyclic nucleic-acid analog joined by phosphodiester bonds.
What is this compound used to make?
It is the parent (S)-GNA cytosine nucleoside: protecting the base and differentiating the two backbone hydroxyls into dimethoxytrityl and phosphoramidite handles gives the (S)-GNA-C phosphoramidite used to add a GNA cytosine during oligonucleotide synthesis.
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