2-O-Acetyl-3,4,5,6-tetra-O-benzyl-d-myo-inosityl diphenylphosphate: A new useful intermediate to inositol phosphate and phospholipids.

Inositol Phosphates / chemistry Phospholipids Stereoisomerism
anti-inflammatory activity desymmetrization l-camphor dimethyl acetal myo-inositol phosphate myo-inositol phospholipids

Journal

Chirality
ISSN: 1520-636X
Titre abrégé: Chirality
Pays: United States
ID NLM: 8914261

Informations de publication

Date de publication:
08 2022
Historique:
received: 04 03 2022
accepted: 23 04 2022
pubmed: 10 5 2022
medline: 15 7 2022
entrez: 9 5 2022
Statut: ppublish

Résumé

Inositol phosphates and inositol phospholipids are ubiquitous in biochemistry and play a central role in cell signaling and regulation events. For this reason, their synthesis has attracted widespread interest. This paper describes the preparation of a new optically active inositol phosphate derivative, 2-O-acetyl-3,4,5,6-tetra-O-benzyl-d-myo-inosityl diphenylphosphate (6), and its characterization by spectroscopic methods. Compound (6) represents a useful intermediate for the preparation of inositol phosphate and phospholipids, in particular of glycerophosphoinositol (GPI), a natural anti-inflammatory agent.

Identifiants

DOI: 10.1002/chir.23457 PMID: 35531652 PMC: PMC9542212
pubmed: 35531652
doi: 10.1002/chir.23457
pmc: PMC9542212
doi:

Substances chimiques

Inositol Phosphates 0
Phospholipids 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

1038-1043

Subventions

Organisme : Innovhub-SSI
Organisme : Cariplo Foundation
ID : 2017-0978

Informations de copyright

© 2022 The Authors. Chirality published by Wiley Periodicals LLC.

Références

Chirality. 2020 Mar;32(3):282-298
pubmed: 31944412
J Biol Chem. 2017 Aug 4;292(31):12828-12841
pubmed: 28600357
Brain Res. 2004 Feb 6;997(2):147-51
pubmed: 14706866
Appl Environ Microbiol. 2017 Aug 1;83(16):
pubmed: 28600316
Org Biomol Chem. 2010 Jan 7;8(1):66-76
pubmed: 20024134
Carbohydr Res. 2003 Apr 22;338(9):999-1001
pubmed: 12681925
Anal Bioanal Chem. 2017 Nov;409(29):6781-6789
pubmed: 28932942
Nat Rev Mol Cell Biol. 2008 Feb;9(2):151-61
pubmed: 18216771
Chirality. 2022 Aug;34(8):1038-1043
pubmed: 35531652
Front Pharmacol. 2019 Oct 11;10:1172
pubmed: 31680956

Auteurs

Sara Sangiorgio (S)

Department of Chemistry, University of Milan, Milan, Italy.

Mattia Cambò (M)

Department of Chemistry, University of Milan, Milan, Italy.

Riccardo Semproli (R)

Department of Drug Sciences, University of Pavia, Pavia, Italy.

Daniela Ubiali (D)

Department of Drug Sciences, University of Pavia, Pavia, Italy.

Giovanna Speranza (G)

Department of Chemistry, University of Milan, Milan, Italy.

Marco Rabuffetti (M)

Department of Chemistry, University of Milan, Milan, Italy.
ORCID: 0000-0003-2089-1333

Articles similaires

Use of dislodgeable foliar residue studies for the evaluation of isomerization potential of active substances for non-dietary risk assessment.

Silke Wagner, Christian J Kuster
1.00
Risk Assessment Plant Leaves Isomerism Humans Stereoisomerism

A temperature-sensitive metabolic valve and a transcriptional feedback loop drive rapid homeoviscous adaptation in Escherichia coli.

Loles Hoogerland, Stefan Pieter Hendrik van den Berg, Yixing Suo et al.
1.00
Escherichia coli Membrane Fluidity Temperature Escherichia coli Proteins Fatty Acids

Roseobacter sinensis sp. nov., a marine bacterium capable to synthesize arachidonic acid.

Hong-Chuan Wang, Meng-Han Huang, Dan-Yuan Guo et al.
1.00
Roseobacter Phylogeny RNA, Ribosomal, 16S Seawater Base Composition

Preparation of D-NCCDs and its application in fluorescent/colorimetric dual-mode discrimination of glutamine enantiomers.

Xuan Liao, Cancan Lu, Yaning Duan et al.
1.00
Glutamine Stereoisomerism Spectrometry, Fluorescence Colorimetry Carbon

Classifications MeSH

questionsmedicales.fr › Glucides › Oses phosphates › Inositol phosphates › 2-O-Acetyl-3,4,5,6-tetra-O-benzyl-d-myo-inosity...
questionsmedicales.fr › Lipides › Lipides membranaires › Phospholipides › 2-O-Acetyl-3,4,5,6-tetra-O-benzyl-d-myo-inosity...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › 2-O-Acetyl-3,4,5,6-tetra-O-benzyl-d-myo-inosity...