1,2,3,4-Tetra-O-acetyl-a-D-glucuronide methyl ester - CAS 5432-32-6
Category:
Carbohydrates
Product Name:
1,2,3,4-Tetra-O-acetyl-a-D-glucuronide methyl ester
Synonyms:
Methyl 1,2,3,4-tetra-O-acetyl-a-D-glucopyranuronate
CAS Number:
5432-32-6
Molecular Weight:
376.31
Molecular Formula:
C15H20O11
COA:
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MSDS:
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Structure:
Monosaccharides
Chemical Structure
CAS 5432-32-6 1,2,3,4-Tetra-O-acetyl-a-D-glucuronide methyl ester

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Reference Reading


1.Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy-droxy-meth-yl-2-tri-chloro-methyl-1,3-dioxolan-4-yl]-2-methyl-prop-2-enoate.
Oishi T1, Yasushima D2, Yuasa K2, Sato T2, Chida N2. Acta Crystallogr E Crystallogr Commun. 2016 Feb 17;72(Pt 3):343-6. doi: 10.1107/S2056989016002474. eCollection 2016.
In the title compound, C10H14Cl3NO5, the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hy-droxy-methyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) Å. There are two intra-molecular hydrogen bonds (O-H⋯N and N-H⋯O) between the hy-droxy and amino groups, so that O- and N-bound H atoms involved in these hydrogen bonds are each disordered with equal occupancies of 0.50. The methyl 2-methyl-prop-2-enoate substituent also shows a disordered structure over two sets of sites with refined occupancies of 0.482 (5) and 0.518 (5). In the crystal, mol-ecules are connected into a dimer by an O-H⋯O hydrogen bond. The dimers are further linked by N-H⋯O, C-H⋯N and C-H⋯O inter-actions, extending a sheet structure parallel to ([Formula: see text]01).
2.Inhibition of Growth by Combined Treatment with Inhibitors of Lactate Dehydrogenase and either Phenformin or Inhibitors of 6-Phosphofructo-2-kinase/Fructose-2,6-bisphosphatase 3.
Lea MA1, Guzman Y2, Desbordes C3. Anticancer Res. 2016 Apr;36(4):1479-88.
Enhanced glycolysis in cancer cells presents a target for chemotherapy. Previous studies have indicated that proliferation of cancer cells can be inhibited by treatment with phenformin and with an inhibitor of 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3 (PFKFB) namely 3-(3-pyridinyl)-1-(4-pyridinyl)-2-propen-1-one (3PO). In the present work, the action of two inhibitors that are effective at lower concentrations than 3PO, namely 1-(3-pyridinyl)-3-(2-quinolinyl)-2-propen-1-one (PQP) and 1-(4-pyridinyl)-3-(2-quinolinyl)-2-propen-1-one (PFK15) were investigated. The inhibitors of lactate dehydrogenase (LDHA) studied in order of half-maximal inhibitory concentrations were methyl 1-hydroxy-6-phenyl-4-(trifluoromethyl)-1H-indole-2-carboxylate (NHI-2) < isosafrole < oxamate. In colonic and bladder cancer cells, additive growth inhibitory effects were seen with the LDHA inhibitors, of which NHI-2 was effective at the lowest concentrations.
3.Comment on "Structural and vibrational studies on 1-(5-Methyl- [1,3,4] thiadiazol-2-yl)-pyrolidin-2-ol" [Spectrochimica Acta Part A, 152 (2016) 252-261]. The importance of intramolecular OH⋯N hydrogen bonding in the conformational properties of thiadiazol-pyrrolidin-2-ol bearing species.
Laurella SL1, Erben MF2. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Jul 5;164:40-2. doi: 10.1016/j.saa.2016.03.018. Epub 2016 Apr 4.
The title paper [1] reports a study on the spectroscopic and physicochemical properties of 1-(5-methyl- [1,3,4]thiadiazol-2-yl)-pyrrolidin-2-ol (MTPN) based on experimental and theoretical data. The latter ones are based on the computed molecular structure for a rather unusual conformer. Here, after a careful analysis of the conformational space of MTPN, the most stable conformation was determined for the molecule isolated in a vacuum, which results to be 21.9kJ/mol more stable than the conformer reported previously. Our study also includes the closely related species 1-(5-trifluoromethyl- [1,3,4]thiadiazol-2-yl)-pyrrolidin-2-ol (FMTPN). An intramolecular OH⋯N hydrogen bond determines the conformational behavior of the [1,3,4]thiadiazol-2-yl)-pyrrolidin-2-ol group as demonstrated by Natural Bond Orbital population analysis.