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L-Guanosine Sale

目录号 : GC66622

L-Guanosine 是 L-构型的 Guanosine。Guanosine 是一种嘌呤核苷,具有抗疱疹病毒活性。

L-Guanosine Chemical Structure

Cas No.:26578-09-6

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产品描述

L-Guanosine is the L-configuration of Guanosine . Guanosine is a purine nucleoside with anti-herpesvirus activity[1][2].

[1]. Du Y, et al. Chirality from D-guanosine to L-guanosine shapes a stable gel for three-dimensional cell culture. Chem Commun (Camb). 2021 Dec 3;57(96):12936-12939.
[2]. De Clercq E. Guanosine analogues as anti-herpesvirus agents. Nucleosides Nucleotides Nucleic Acids. 2000 Oct-Dec;19(10-12):1531-41.

Chemical Properties

Cas No. 26578-09-6 SDF Download SDF
分子式 C10H13N5O5 分子量 283.24
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1 mM 3.5306 mL 17.6529 mL 35.3057 mL
5 mM 0.7061 mL 3.5306 mL 7.0611 mL
10 mM 0.3531 mL 1.7653 mL 3.5306 mL
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Research Update

Chirality from D-guanosine to L-Guanosine shapes a stable gel for three-dimensional cell culture

Chem Commun (Camb) 2021 Dec 3;57(96):12936-12939.PMID:34734933DOI:10.1039/c9cc09911e.

It is proved that L-Guanosine (L-G) as an enantiomer of D-guanosine (D-G) forms more stable gels than D-G, suggesting that alteration of chirality may be a new strategy for improving the lifetime stability of supramolecular hydrogels. Experiments for three-dimensional cell culture reveal that the L-G gel is a candidate for the extracellular matrix.

Oligomerization of activated D- and L-Guanosine mononucleotides on templates containing D- and L-deoxycytidylate residues

Proc Natl Acad Sci U S A 1998 Nov 10;95(23):13448-52.PMID:9811820DOI:10.1073/pnas.95.23.13448.

The oligomerization of activated D- and L- and racemic guanosine-5'-phosphoro-2-methylimidazole on short templates containing D- and L-deoxycytidylate has been studied. Results obtained with D-oligo(dC)s as templates are similar to those previously reported for experiments with a poly(C) template. When one L-dC or two consecutive L-dCs are introduced into a D-template, regiospecific synthesis of 3'-5' oligo(G)s proceeds to the end of the template, but three consecutive L-dCs block synthesis. Alternating D-,L-oligomers do not facilitate oligomerization of the D-, L-, and racemic 2-guanosine-5'-phosphoro-2-methylimidazole. We suggest that once a "predominately D-metabolism" existed, occasional L-residues in a template would not have led to the termination of self-replication.

Derivatives of L-adenosine and L-Guanosine as substrates for human deoxycytidine kinase

Nucleosides Nucleotides 1999 Apr-May;18(4-5):857-60.PMID:10432694DOI:10.1080/15257779908041581.

A series of analogues of L-adenosine and of L-Guanosine, including beta-L-dA, beta-L-Ado, beta-L-araA, and beta-L-dG, have been shown to be substrates of human deoxycytidine kinase thus demonstrating the complete lack of enantioselectivity of this enzyme.

Chiral selection in poly(C)-directed synthesis of oligo(G)

Nature 1984 Aug;310(5978):602-4.PMID:6462250DOI:10.1038/310602a0.

Theories of the origin of optical asymmetry in living systems place fundamental importance on the amplification of optical asymmetry by an autocatalytic process. The replication of a polynucleotide is one obvious choice for such an autocatalytic growth mechanism. If an optically homogeneous polynucleotide could replicate by directing the polymerization of monomers of the same handedness, while excluding monomers of the opposite handedness, its chiral descendants would come to dominate what was once an achiral environment. Recently, two highly efficient template-directed reaction systems have been developed for the oligomerization of activated guanosine mononucleotides (Fig. 1) on a poly(C) template. The synthesis of L-Guanosine 5'-mononucleotide makes it possible to study chiral selection in these systems. We report here that poly(C)-directed oligomerization of activated guanosine mononucleotides proceeds readily if the monomers are of the same optical handedness as the template, and is indeed far less efficient if the monomers are of the opposite handedness. However, in template-directed reactions with a racemic mixture, monomers of the opposite handedness to the template are incorporated as chain terminators at the 2'(3') end of the products. This inhibition raises an important problem for many theories of the origin of life.

Low enantioselectivities of human deoxycytidine kinase and human deoxyguanosine kinase with respect to 2'-deoxyadenosine, 2'-deoxyguanosine and their analogs

Biochimie 1999 Nov;81(11):1041-7.PMID:10575360DOI:10.1016/s0300-9084(99)00331-4.

The antiviral activity of L-nucleoside analogs depends in part on the enantioselectivity of nucleoside kinases which catalyse their monophosphorylation. The substrate properties of human recombinant deoxycytidine kinase (dCK) and human recombinant deoxyguanosine kinase (dGK) with respect to L-adenosine and L-Guanosine analogs, in the presence of saturating amounts of ATP and relatively high concentrations of substrates, demonstrated a marked lack of enantioselectivity of both these enzymes. Human dCK catalysed the phosphorylation of D- and L-enantiomers of beta-dA, beta-araA, and beta-dG with enantioselectivities favoring the unnatural enantiomer for the adenosine derivatives and the natural enantiomer for 2'-deoxyguanosine. No other tested L-adenosine or L-Guanosine analog was a substrate of dCK. Similarly, D- and L-enantiomers of beta-dA, beta-araA, and beta-dG were substrates of human dGK but with different enantioselectivities compared to dCK, especially concerning beta-dA. The present results indicate that human dCK and dGK have similar properties including substrate properties, relaxed enantioselectivities, and possibly catalytic cycles.