93134-41-9

Basic information

• Product Name: Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate)
• Synonyms: N-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine;3'-O-Levulinyl--N2-isobutyryl-2'-deoxyguanosine;4-Oxo-pentanoic acid (2R,3S,5R)-2-hydroxymethyl-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester;5'-OH-dGi-Bu-3'-O-Lev;3'-O-Levulinyl-N2-isobutyryl-2'-deoxyguanosine
• CAS NO: 93134-41-9
• Molecular Formula: C19H25N5O7
• Molecular Weight: 435.43100
• Mol File: 93134-41-9.mol

Chemical Properties

• Density: 1.56±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate)(CAS DataBase Reference)
• NIST Chemistry Reference: Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate)(93134-41-9)
• EPA Substance Registry System: Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate)(93134-41-9)

Safety Data

• Hazardous Substances Data: 93134-41-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate) is used as a protected nucleotide derivative for the synthesis of nucleic acids and development of new drugs targeting various diseases.
Used in Research and Development:
Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate) is used as a building block in the development of new chemical entities and the study of nucleic acid structure and function.
Used in Diagnostics:
Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate) can be used as a component in the development of diagnostic tools for detecting and monitoring diseases at the molecular level.
Used in Biochemical Applications:
Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-, 3'-(4-oxopentanoate) can be used in various biochemical applications, such as the study of enzyme mechanisms, the development of new biochemical assays, and the investigation of nucleic acid interactions with proteins and other molecules.

Upstream product

• 591-12-8 5-methyl-2-furanone 
• 440327-43-5 N-isobutyryl-3',5'-di-O-levulinyl-2'-deoxyguanosine 
• 68892-42-2 N-isobutyryl-2'-deoxyguanosine 
• 123-76-2 levulinic acid 
• 68892-41-1 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine 
• 647834-80-8 O-levulinyl acetonoxime 
• 86710-51-2 4-Oxo-pentanoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 

Downstream Products

• 93134-56-6 C₅₀H₅₇N₁₀O₁₄P 
• 195826-30-3 4-Oxo-pentanoic acid (2R,3S,5R)-2-[diisopropylamino-(4-nitro-phenoxy)-phosphanyloxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 656249-33-1 C₅₇H₆₄N₁₁O₁₅PS 
• 656249-24-0 C₅₃H₅₉N₈O₁₅PS 
• 656249-30-8 5'-O-DMTr-dC^Bzps_CNEdG^i-Bu-3'-O-Lev 
• 152998-05-5 N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-cytidine 3'-(2-cyanoethylphosphonate) 
• 160107-22-2 N₂-isobutyryl-3'-O-(2-cyanoethyl)-phosphonate-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine 
• 656249-32-0 C₅₇H₆₄N₁₁O₁₅P 
• 224186-78-1 C₅₃H₅₉N₈O₁₅P 
• 93134-54-4 Phosphoric acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester methyl ester 
• 93134-55-5 C₅₂H₅₅N₈O₁₄P 
• 93134-57-7 C₄₆H₅₂N₇O₁₄P 
• 93134-47-5 C₅₁H₅₈N₇O₁₆P 

Relevant articles and documents

Enzymatic parallel kinetic resolution of mixtures of d / l 2′-deoxy and ribonucleosides: An approach for the isolation of β- L -nucleosides

We have developed a lipase-catalyzed parallel kinetic resolution of mixtures of β-d/l-nucleosides. The opposite selectivity during acylation exhibited by Pseudomonas cepacia lipase (PSL-C) with β-d- and β-l-nucleosides furnished acylated compounds that have different R f values. As a consequence, isolation of both products was achieved by simple column chromatography. Computer modeling of the transition-state analogues during acylation of β-d- and β-l-2′-deoxycytidine with PSL-C was carried out to explain the high selectivity. PSL-C favored the 3′-O-levulination of the β-d enantiomer, whereas the 5′-OH group was acylated in 2′-deoxy-β-l-cytidine. In both cases, the cytosine base was placed in the alternate hydrophobic pocket of PSLs substrate-binding site, where it can form extra hydrogen bonds (in addition to the five essential catalytically relevant hydrogen bonds) that stabilize these intermediates catalyzing the selective acylation of β-d/l-nucleosides.

2,2,5,5-Tetramethylpyrrolidin-3-one-1-sulfinyl group for 5′-hydroxyl protection of deoxyribonucleoside phosphoramidites in the solid-phase preparation of DNA oligonucleotides

Several nitrogen-sulfur reagents have been investigated as potential 5′-hydroxyl protecting groups for deoxyribonucleoside phosphoramidites to improve the synthesis of oligonucleotides on glass microarrays. Out of the nitrogen-sulfur-based protecting grou

Novel enzymatic synthesis of levulinyl protected nucleosides useful for solution phase synthesis of oligonucleotides

An efficient synthesis of 3′- and 5′-O-levulinyl-2′- deoxy- and 2′-O-alkylribonucleosides has been developed from appropriate nucleosides by enzyme-catalyzed regioselective acylation in organic solvents. Several lipases were screened in combination with a

Building blocks for the solution phase synthesis of oligonucleotides: Regioselective hydrolysis of 3′,5′-di-O-levulinylnucleosides using an enzymatic approach

A short and convenient synthesis of 3′- and 5′-O-levulinyl-2′-deoxynucleosides has been developed from the corresponding 3′,5′-di-O-levulinyl derivatives by regioselective enzymatic hydrolysis, avoiding several tedious chemical protection/deprotection steps. Thus, Candida antartica lipase B (CAL-B) was found to selectively hydrolyze the 5′-levulinate esters, furnishing 3′-O-levulinyl-2′-deoxynucleosides 3 in >80% isolated yields. On the other hand, immobilized Pseudomonas cepacia lipase (PSL-C) and Candida antarctica lipase A (CAL-A) exhibit the opposite selectivity toward the hydrolysis at the 3′-position, affording 5′-O-levulinyl derivatives 4 in >70% yields. A similar hydrolysis procedure was successfully extended to the synthesis of 3′- and 5′-O-levulinyl-protected 2′-O-alkylribonucleosides 7 and 8. This work demonstrates for the first time application of commercial CAL-B and PSL-C toward regioselective hydrolysis of levulinyl esters with excellent selectivity and yields. It is noteworthy that protected cytidine and adenosine base derivatives were not adequate substrates for the enzymatic hydrolysis with CAL-B, whereas PSL-C was able to accommodate protected bases during selective hydrolysis. In addition, we report an improved synthesis of dilevulinyl esters using a polymer-bound carbodiimide as a replacement for dicyclohexylcarbodiimide (DCC), thus considerably simplifying the workup for esterification reactions.

Synthesis of oligonucleotides

Synthetic processes are provided for the solution phase synthesis of oligonucleotides, especially phosphorothioate oligonucleotides, and intermediate compounds useful in the processes. Intermediates having structure (I) are prepared in accordance with preferred embodiments.

Process for the synthesis of oligomeric compounds

Synthetic processes are provided wherein oligomeric compounds are prepared having phosphodiester, phosphorothioate, and phosphorodithioate covalent linkages. Also provided are synthetic intermediates useful in the processes.

Oligodeoxyribonucleotide phosphorothioates: Substantial reduction of (N- 1)-mer content through the use of trimeric phosphoramidite synthons

Use of fully protected trimeric phosphoramidite synthons in the synthesis of oligonucleotide phosphorothioate shows a substantial reduction (>85%) in (n-1)-mer content as compared to oligomers synthesized through coupling of standard phosphoramidite monom

Oligomeric phosphite, phosphodiester, Phosphorothioate and phosphorodithioate compounds and intermediates for preparing same

Synthetic processes are provided wherein oligomeric compounds are prepared having phosphodiester, phosphorothioate, and phosphorodithioate covalent linkages. Also provided are synthetic intermediates useful in such processes.

On the formation of longmers in phosphorothioate oligodeoxyribonucleotide synthesis

The extent of longmer formation in phosphorothioate oligodeoxyribonucleotide synthesis through amidite chemistry on solid support depends on base composition, contact time and acidity of the promoter used for activation of the phosphoramidite. A longmer f

Improvements in Oligodeoxyribonucleotide Synthesis: Methyl N,N-Dialkylphosphoramidite Dimer Units for Solid Support Phosphite Methodology

Two procedures for the synthesis of methyl N,N-dialkylphosphoramidite dinucleotides (dimer units) compatible with the current solid support phosphite methodology of oligodeoxynucleotide synthesis are described for the first time.In the first procedure a c