Guanosine 5'-monophosphate - CAS 85-32-5

Guanosine 5'-monophosphate is a purine ribonucleoside 5'-monophosphate having guanine as the nucleobase. It has a role as a metabolite, a biomarker, an Escherichia coli metabolite and a mouse metabolite. It is a guanosine 5'-phosphate and a purine ribonucleoside 5'-monophosphate. It is a conjugate acid of a guanosine 5'-monophosphate(2-). Guanosine 5 '-monophosphate is a guanine nucleotide containing one phosphate group, which is esterified into the sugar moiety and widely found in nature.

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Molecular Formula
C10H14N5O8P
Molecular Weight
363.22

Guanosine 5'-monophosphate

    • Specification
      • Related CAS
        146894-16-8 (disodium salt hydrate) 5550-12-9 (disodium salt)
        Purity
        ≥95%
        Solubility
        Soluble in Ethanol (Practically insoluble), Water (Slightly, Sonicated)
        Appearance
        Odourless, colourless or white crystals or white crystalline powder
        Storage
        Store at -20 °C, under inert atmosphere
        IUPAC Name
        [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
        Synonyms
        5-Guanylic Acid; 5'-GMP; GMP; Guanidine Monophosphate; Guanosine 5'-Phosphate; Guanosine 5'-Phosphoric Acid; Guanosine Monophosphate; Guanylic Acid
    • Properties
      • Boiling Point
        64.0 °C at 0.05 Torr
        Melting Point
        91-93 °C
        Density
        2.47±0.10 g/cm3
        InChI Key
        RQFCJASXJCIDSX-UUOKFMHZSA-N
        InChI
        InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
        Canonical SMILES
        C1=NC2=C(N1C3C(C(C(O3)COP(=O)(O)O)O)O)N=C(NC2=O)N
        Stability
        Stable under recommended storage conditions.
    • Reference Reading
      • 1.Guanine-centric self-assembly of nucleotides in water: an important consideration in prebiotic chemistry.
        Cassidy LM1, Burcar BT, Stevens W, Moriarty EM, McGown LB. Astrobiology. 2014 Oct;14(10):876-86. doi: 10.1089/ast.2014.1155. Epub 2014 Oct 6.
        Investigations of plausible prebiotic chemistry on early Earth must consider not only chemical reactions to form more complex products such as proto-biopolymers but also reversible, molecular self-assembly that would influence the availability, organization, and sequestration of reactant molecules. The self-assembly of guanosine compounds into higher-order structures and lyotropic liquid crystalline "gel" phases through formation of hydrogen-bonded guanine tetrads (G-tetrads) is one such consideration that is particularly relevant to an RNA-world scenario. G-tetrad-based gelation has been well studied for individual guanosine compounds and was recently observed in mixtures of guanosine with 5'-guanosine monophosphate (GMP) as well. The present work investigates the self-assembly of GMP in the presence of the other RNA nucleotides. Effects of the total concentration and relative proportion of the nucleotides in the mixtures, the form (disodium salt vs.
        2.5'-Guanosine monophosphate mediated biocompatible porous hydrogel of β-FeOOH-viscoelastic behavior, loading, and release capabilities of freeze-dried gel.
        Kumar A1, Gupta SK. J Phys Chem B. 2014 Sep 4;118(35):10543-51. doi: 10.1021/jp5038427. Epub 2014 Aug 21.
        The present manuscript reports the characterization, optimization of rheological properties, and loading and release capabilities of 5'-GMP mediated β-FeOOH hydrogel. Circular dichroism (CD) analysis indicates it to contain mainly the left-handed helix similar to that of Z-DNA. The highest viscosity (>300 cP) corresponds to the sample containing 2.5 × 10(-3) mol dm(-3) of 5'-GMP (SP2H). Field emission scanning electron microscope (FESEM) and transmission electron microscope (TEM) studies indicate the freeze-dried (FD) SP2H to be porous in nature, which is also supported by its high Brunauer-Emmett-Teller (BET) surface area of 226 m(2)/g as compared to that of SP3H (75 m(2)/g). Selected area electron diffraction (SAED) analysis and Raman spectroscopy show it to contain β-FeOOH phase. The FD SP2H exhibits the high swelling ratio (326%) and loading capacity for methylene blue (MB) dye. It displays a controlled and efficient release (>90%) for optimized [MB] (2.
        3.Therapeutic targets for treating fibrotic kidney diseases.
        Lee SY1, Kim SI2, Choi ME3. Transl Res. 2015 Apr;165(4):512-30. doi: 10.1016/j.trsl.2014.07.010. Epub 2014 Aug 13.
        Renal fibrosis is the hallmark of virtually all progressive kidney diseases and strongly correlates with the deterioration of kidney function. The renin-angiotensin-aldosterone system blockade is central to the current treatment of patients with chronic kidney disease (CKD) for the renoprotective effects aimed to prevent or slow progression to end-stage renal disease (ESRD). However, the incidence of CKD is still increasing, and there is a critical need for new therapeutics. Here, we review novel strategies targeting various components implicated in the fibrogenic pathway to inhibit or retard the loss of kidney function. We focus, in particular, on antifibrotic approaches that target transforming growth factor (TGF)-β1, a key mediator of kidney fibrosis, and exciting new data on the role of autophagy. Bone morphogenetic protein (BMP)-7 and connective tissue growth factor (CTGF) are highlighted as modulators of profibrotic TGF-β activity.
        4.Impact of high hydrostatic pressure on non-volatile and volatile compounds of squid muscles.
        Yue J1, Zhang Y1, Jin Y1, Deng Y2, Zhao Y3. Food Chem. 2016 Mar 1;194:12-9. doi: 10.1016/j.foodchem.2015.07.134. Epub 2015 Jul 29.
        The effects of high hydrostatic pressure processing (HHP at 200, 400 or 600MPa) on non-volatile and volatile compounds of squid muscles during 10-day storage at 4°C were investigated. HHP increased the concentrations of Cl(-) and volatile compounds, reduced the level of PO4(3-), but did not affect the contents of 5'-uridine monophosphate (UMP), 5'-guanosine monophosphate (GMP), 5'-inosine monophosphate (IMP), Na(+) and Ca(2+) in squids on Day 0. At 600MPa, squids had the highest levels of 5'-adenosine monophosphate, Cl(-) and lactic acid, but the lowest contents of CMP and volatile compounds on Day 10. Essential free amino acids and succinic acids were lower on Day 0 than on Day 10. HHP at 200MPa caused higher equivalent umami concentration (EUC) on Day 0, and the EUC decreased with increasing pressure on Day 10. Generally, HHP at 200MPa was beneficial for improving EUC and volatile compounds of squids.
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