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Search for "glucuronide" in Full Text gives 4 result(s) in Beilstein Journal of Organic Chemistry.
Anomeric modification of carbohydrates using the Mitsunobu reaction
Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138
- stereoselective coupling of an allyl glucuronide, in which all hydroxy groups except the anomeric OH were O-acyl-protected, with carboxylic acids by a Mitsunobu reaction [35]. The reaction was successful even when a free phenolic function was present in the employed acid and the desired β-anomer of the 1-O-acyl-β
- -D-glucuronide products could be isolated in up to 50% yield. Similarly, regioselective esterification of unprotected allyl glucuronide 11 was performed by Juteau et al. with the acids 12–16 yielding anomeric mixtures of the respective 1-O-acyl-β-D-glucuronides 18–22 in quite acceptable yields even
Synthesis and stability study of a new major metabolite of γ-hydroxybutyric acid
Beilstein J. Org. Chem. 2013, 9, 641–646, doi:10.3762/bjoc.9.72
- glucuronidation approach that provides GHB glucuronide 2 and a deuterium-labelled analogue d4-2 of high purity suitable for analytical chemistry. In addition, we have assessed the stability of GHB glucuronide 2 by mimicking the natural pH range for urine, which is of importance in the development of new
- analytical methods. Using NMR we show that GHB glucuronide 2 is highly stable towards aqueous hydrolysis within the pH range normally observed for urine even at elevated temperature. Keywords: analytical chemistry; cabohydrate chemistry; forensic chemistry; glucuronide; γ-hydroxybutyric acid; metabolite
- as alcohols and carboxylic acids to their respective glucuronides (e.g., Figure 1). Glucuronides generally have longer plasma half-life values than the unmodified compound (e.g., ethyl glucuronide versus ethanol), making it possible to use the glucuronide as a biomarker to extend the analytical
Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin
Beilstein J. Org. Chem. 2012, 8, 705–711, doi:10.3762/bjoc.8.79
- cells, wherein the 3-(2-thioethyl)-N-acetylamino- and 3-(2-thioethyl)-thio-linked glucuronide derivatives were effective inhibitors with IC50 values as low as 54 µM. Keywords: antiviral activity; carbenoxolone; glycyrrhizin; influenza A virus; thioglycoside; triterpene; Introduction The triterpene
- (structure not shown). The secondary amino group in compound 8 was subjected to further derivatization by N-acetylation (triethylamine, acetic anhydride), which gave compound 9 in 96% yield. Deprotection of the ethyl 1-thio-glucuronide derivatives 8 and 9 was achieved by acid-catalyzed cleavage of the
- diphenylmethyl ester group with TFA/anisole (as carbocation scavenger), giving the monoacid derivatives 10 and 11 in 75% and 89% yield, respectively. Subsequent transesterification of 10 and 11 with methanolic NaOMe afforded the deacetylated methyl ester glucuronide derivatives 12 and 14, respectively, which
An efficient partial synthesis of 4′-O-methylquercetin via regioselective protection and alkylation of quercetin
Beilstein J. Org. Chem. 2009, 5, No. 60, doi:10.3762/bjoc.5.60
- ), mainly conjugated as glucuronides or sulfates [8], are present. With some variations in the relative abundance of the methylation positions, the same metabolism was also observed in rat [9] and in vivo cell cultures [10]. As the glucuronide or sulfate groups are readily deconjugated in tissues [11
- functions such as sulfate or glucuronide groups. These compounds will allow structure–activity relationship studies of flavonoids to be carried out. Their easily obtained labeled forms will give access to isotopic dilution dosage by LC-MS or LC-MS/MS and will help in the identification of unknown flavonoid
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