Niyonsaba, Edouard’s team published research in Analytical Chemistry (Washington, DC, United States) in 91 | CAS: 267244-08-6

Analytical Chemistry (Washington, DC, United States) published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Name: (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Niyonsaba, Edouard published the artcileDifferentiation of Deprotonated Acyl-, N-, and O-Glucuronide Drug Metabolites by Using Tandem Mass Spectrometry Based on Gas-Phase Ion-Molecule Reactions Followed by Collision-Activated Dissociation, Name: (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, the publication is Analytical Chemistry (Washington, DC, United States) (2019), 91(17), 11388-11396, database is CAplus and MEDLINE.

Glucuronidation, a common phase II biotransformation reaction, is one of the major in vitro and in vivo metabolism pathways of xenobiotics. In this process, glucuronic acid is conjugated to a drug or a drug metabolite via a carboxylic acid, a hydroxy, or an amino group to form acyl, O-, and/or N-glucuronide metabolites, resp. This process is traditionally thought to be a detoxification pathway. However, some acyl glucuronides react with biomols. in vivo, which may result in immune-mediated idiosyncratic drug toxicity (IDT). In order to avoid this, one may attempt in early drug discovery to modify the lead compounds in such a manner that they then have a lower probability of forming reactive acyl glucuronide metabolites. Because most drugs or drug candidates bear multiple functionalities, e.g., hydroxy, amino, and carboxylic acid groups, glucuronidation can occur at any of those. However, differentiation of isomeric acyl, N- and O-glucuronide derivatives of drugs is challenging. In this study, gas-phase ion-mol. reactions between deprotonated glucuronide metabolites and BF3 followed by collision-activated dissociation (CAD) in a linear quadrupole ion trap mass spectrometer were demonstrated to enable the differentiation of acyl, N-, and O-glucuronides. Only deprotonated N-glucuronides and deprotonated, migrated acyl glucuronides form the two diagnostic product ions: a BF3 adduct that has lost two HF mols., [M – H + BF3-2 HF]-, and an adduct formed with two BF3 mols. that has lost three HF mols., [M – H + 2 BF3-3 HF]-. These product ions were not observed for deprotonated O-glucuronides and unmigrated, deprotonated acyl glucuronides. Upon CAD of the [M – H + 2 BF3-3 HF]- product ion, a diagnostic fragment ion is formed via the loss of 2-fluoro-1,3,2-dioxaborale (MW of 88 Da) only in the case of deprotonated, migrated acyl glucuronides. Therefore, this method can be used to unambiguously differentiate acyl, N- and O-glucuronides. Further, coupling this method-ol. with HPLC enables the differentiation of unmigrated 1-β-acyl glucuronides from the isomeric acyl glucuronides formed upon acyl migration. Quantum chem. calculations at the M06-2X/6-311++G(d,p) level of theory were employed to probe the mechanisms of the reactions of interest.

Analytical Chemistry (Washington, DC, United States) published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Name: (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics