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362-76-5

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362-76-5 Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 362-76-5 differently. You can refer to the following data:
1. A useful precursor for the preparation of nucleic acids.
2. 2',3'-O-Isopropylideneguanosine is a useful precursor for the preparation of nucleic acids

Check Digit Verification of cas no

The CAS Registry Mumber 362-76-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,6 and 2 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 362-76:
(5*3)+(4*6)+(3*2)+(2*7)+(1*6)=65
65 % 10 = 5
So 362-76-5 is a valid CAS Registry Number.

362-76-5 Well-known Company Product Price

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  • TCI America

  • (I0703)  2',3'-O-Isopropylideneguanosine  >98.0%(HPLC)(T)

  • 362-76-5

  • 5g

  • 690.00CNY

  • Detail

362-76-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2',3'-O-Isopropylideneguanosine

1.2 Other means of identification

Product number -
Other names 2',3'-O-ISOPROPYLIDENE-GUANOSINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:362-76-5 SDS

362-76-5Relevant articles and documents

Phosphate-modified analogues of m7GTP and m7Gppppm7G - Synthesis and biochemical properties

Ziemniak, Marcin,Kowalska, Joanna,Lukaszewicz, Maciej,Zuberek, Joanna,Wnek, Katarzyna,Darzynkiewicz, Edward,Jemielity, Jacek

, p. 5369 - 5381 (2015)

The synthesis and biochemical properties of 17 new mRNA cap analogues are reported. Six of these nucleotides are m7GTP derivatives, whereas 11 are 'two headed' tetraphosphate dinucleotides based on a m7Gppppm7G structure. The compounds contain either a boranophosphate or phosphorothioate moiety in the nucleoside neighbouring position(s) and some of them possess an additional methylene group between β and γ phosphorus atoms. The compounds were prepared by divalent metal chloride-mediated coupling of an appropriate m7GMP analogue with a given P1,P2-di(1-imidazolyl) derivative. The analogues were evaluated as tools for studying cap-dependent processes in a number of biochemical assays, including determination of affinity to eukaryotic initiation factor eIF4E, susceptibility to enzymatic hydrolysis, and translational efficiency in vitro. The results indicate that modification in the phosphate chain can increase binding to cap-interacting proteins and provides higher resistance to degradation. Furthermore, modified derivatives of m7GTP were found to be potent inhibitors of cap-dependent translation in cell free systems.

Release of bioactive volatiles from supramolecular hydrogels: Influence of reversible acylhydrazone formation on gel stability and volatile compound evaporation

Buchsnee Levrand, Barbara,Fieber, Wolfgang,Vigouroux-Elie, Florence,Sreenivasachary, Nampally,Lehn, Jean-Marie,Herrmann, Andreas

, p. 2906 - 2919 (2011)

In the presence of alkali metal cations, guanosine-5′-hydrazide (1) forms stable supramolecular hydrogels by selective self-assembly into a G-quartet structure. Besides being physically trapped inside the gel structure, biologically active aldehydes or ketones can also reversibly react with the free hydrazide functions at the periphery of the G-quartet to form acylhydrazones. This particularity makes the hydrogels interesting as delivery systems for the slow release of bioactive carbonyl derivatives. Hydrogels formed from 1 were found to be significantly more stable than those obtained from guanosine. Both physical inclusion of bioactive volatiles and reversible hydrazone formation could be demonstrated by indirect methods. Gel stabilities were measured by oscillating disk rheology measurements, which showed that thermodynamic equilibration of the gel is slow and requires several cooling and heating cycles. Furthermore, combining the rheology data with dynamic headspace analysis of fragrance evaporation suggested that reversible hydrazone formation of some carbonyl compounds influences the release of volatiles, whereas the absolute stability of the gel seemed to have no influence on the evaporation rates.

Synthesis of three regioisomeric (7-methoxychromenonyl)methyl guanosine 5′-phosphates

Faurel-Paul, Elodie,Yoshida, Kenta,Sepulcre, Magali,Dhimane, Hamid,Merrer, Yves Le

, p. 459 - 474 (2009)

Herein we describe the synthesis of three new (7-methoxychromenonyl)methyl 2-N-propionyl-2′,3′-isopropylideneguanosine 5′-phosphate diesters, potentially photolabile nucleotides, via an H-phosphonate strategy. The stability of these compounds toward acidic and basic conditions was evaluated during the nucleoside moiety deprotection. Copyright Taylor & Francis Group, LLC.

Modified GSMP synthesis greatly improves the disulfide crosslink of T7 run-off siRNAs with cell penetrating peptides

Schmitz, Katja,Hahn, Frank,Schepers, Ute

, p. 2959 - 2963 (2010)

Preventing intramolecular cyclization greatly improves 5′-deoxy- 5′-thioguanosine monophosphorothioate (GSMP) synthesis and its application as a potent initiator nucleotide for T7 run-off transcription of noncoding RNAs. GSMP was efficiently incorporated into the 5′-end of siRNA sense strands and the resulting thiol-modified siRNA was crosslinked with a free cysteine of cell penetrating peptide Penetratin as monitored by mass spectrometry. Cellular uptake and the knockdown potential of the peptide-coupled siRNA (pepsiRNA) were evaluated in primary cells. Georg Thieme Verlag Stuttgart - New York.

Nucleotide substrate specificity of anti-hepatitis C virus nucleoside analogs for human mitochondrial RNA polymerase

Ehteshami, Maryam,Zhou, Longhu,Amiralaei, Sheida,Shelton, Jadd R.,Cho, Jong Hyun,Zhang, Hongwang,Li, Hao,Lu, Xiao,Ozturk, Tugba,Stanton, Richard,Amblard, Franck,McBrayer, Tamara R.,Coats, Steven J.,Schinazi, Raymond F.

, (2017)

Nucleoside analog inhibitors (NAIs) are an important class of antiviral agents. Although highly effective, some NAIs with activity against hepatitis C virus (HCV) can cause toxicity, presumably due to off-target inhibition of host mitochondrial RNA polymerase (POLRMT). The in vitro nucleotide substrate specificity of POLRMT was studied in order to explore structure-activity relationships that can facilitate the identification of nontoxic NAIs. These findings have important implications for the development of all anti-RNA virus NAIs.

Synthesis and evaluation of potential inhibitors of eIF4E cap binding to 7-methyl GTP

Ghosh, Phalguni,Park, Chunkyung,Peterson, Mark S.,Bitterman, Peter B.,Polunovsky, Vitaly A.,Wagner, Carston R.

, p. 2177 - 2180 (2005)

Cap-dependent translation is initiated by the binding of eIF4E to capped mRNA (m7GpppN). We have prepared a small library of 7-methyl guanosine nucleoside and nucleotide analogs and evaluated their ability to inhibit eIF4E binding to 7-methyl GTP with a competitive eIF4E binding immunoassay. 5′-H-Phosphonate derivatives in which the 2′- and 3′-riboside hydroxyls were tethered together by an isopropylidene group were shown to be a new class of inhibitors of eIF4E binding to capped mRNA.

From G-quartets to G-ribbon gel by concentration and sonication control

Meng, Luyan,Liu, Keyin,Mo, Shuli,Mao, Yueyuan,Yi, Tao

, p. 1525 - 1532 (2013)

Two guanosine analogues have been designed and synthesized by connecting one (1) or three adamantane branches (2). The compound containing a single adamantane branch formed G-quartets in acetonitrile solution, and was then transformed into a G-ribbon gel at concentrations higher than the critical gelation concentration. In contrast, the compound with three adamantane branches precipitated after a heating-cooling process. By means of circular dichroism and UV/visible spectra, NMR, SEM, and structural studies, the mechanism of the formation of the G-quartets and G-ribbon gel, as well as the difference in the self-assembly modes of the two compounds, have been fully elucidated. Compound 1 firstly self-assembled into G-quartets in solutions in the concentration range 5.0 × 10-4 to 1.0 × 10-2 M, and these G-quartets were transformed into a G-ribbon on further increasing the concentration. Gelation occurred when the G-ribbon self-assembled into a hexagonal columnar structure with the help of intermolecular hydrogen-bonding and hydrophobic interactions. This gel was sensitive to sonication and underwent a morphology change from a columnar structure to a flower-like structure composed of flakes. In contrast, due to steric hindrance, compound 2 only assembled into a spherical structure based on hydrophobic interactions.

Kinase-Inhibitory Nucleoside Derivatives from the Pacific Bryozoan Nelliella nelliiformis

Bracegirdle, Joe,Gordon, Dennis P.,Harvey, Joanne E.,Keyzers, Robert A.

, p. 547 - 551 (2020/03/19)

Marine organisms are a valuable source of bioactive natural products, yet bryozoan invertebrates have been relatively understudied. Herein, we report nelliellosides A and B, new secondary metabolites of the Pacific bryozoan Nelliella nelliiformis, found using NMR-guided isolation. Their structures, including absolute configurations, were elucidated using spectroscopic and chromatographic techniques. Total synthesis of the natural products and four analogues was also achieved, in addition to an assessment of their biological activity, especially kinase inhibition.

Corroboration of Zn(ii)-Mg(ii)-tertiary structure interplays essential for the optimal catalysis of a phosphorothiolate thiolesterase ribozyme

Wang, Tzu-Pin,Su, Yu-Chih,Chen, Yi,Severance, Scott,Hwang, Chi-Ching,Liou, Yi-Ming,Lu, Chia-Hui,Lin, Kun-Liang,Zhu, Rui Jing,Wang, Eng-Chi

, p. 32775 - 32793 (2018/10/15)

The TW17 ribozyme, a catalytic RNA selected from a pool of artificial RNA, is specific for the Zn2+-dependent hydrolysis of a phosphorothiolate thiolester bond. Here, we describe the organic synthesis of both guanosine α-thio-monophosphate and the substrates required for selecting and characterizing the TW17 ribozyme, and for deciphering the catalytic mechanism of the ribozyme. By successively substituting the substrate originally conjugated to the RNA pool with structurally modified substrates, we demonstrated that the TW17 ribozyme specifically catalyzes phosphorothiolate thiolester hydrolysis. Metal titration studies of TW17 ribozyme catalysis in the presence of Zn2+ alone, Zn2+ and Mg2+, and Zn2+ and [Co(NH3)6]3+ supported our findings that Zn2+ is absolutely required for ribozyme catalysis, and indicated that optimal ribozyme catalysis involves the presence of outer-sphere and one inner-sphere Mg2+. A survey of the TW17 ribozyme activity at various pHs revealed that the activity of the ribozyme critically depends on the alkaline conditions. Moreover, a GNRA tetraloop-containing ribozyme constructed with active catalysis in trans provided catalysis and multiple substrate turnover efficiencies significantly higher than ribozymes lacking a GNRA tetraloop. This research supports the essential roles of Zn2+, Mg2+, and a GNRA tetraloop in modulating the TW17 ribozyme structure for optimal ribozyme catalysis, leading also to the formulation of a proposed reaction mechanism for TW17 ribozyme catalysis.

SULFAMIDE AND SULFAMATE INHIBITORS OF hHint1

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Page/Page column 0126, (2018/03/25)

Embodiments provide, among things, compounds of the formula I and methods for using such compounds to reduce pain (e.g., neuronal pain), treat a mammal's addiction to nicotine or anti-pain drugs, and increase a mammal's sensitivity to drugs that bind MOR or NMDAR.

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