title: Biology and chemistry of neuroprostanes. First total synthesis of 17-A4-NeuroP: validation of a convergent strategy to a number of cyclopentenone neuroprostanes.
abstract: In a process associated with ageing and neurodegeneration, radical peroxidation of docosahexaenoic acid (DHA) in neurons affords a multitude of prostaglandin-like neuroprostanes in a non-regioselective and non-stereoselective manner. In this paper, the synthesis of racemic 17-A4-NeuroP and 14-A4-NeuroP validated a general approach to several regioisomeric cyclopentenone A4- and J4-NeuroPs needed for biological tests. In preliminary experiments 17-A4-NeuroP, in analogy with 14-A4-NeuroP, readily adducted GSH free thiol, suggesting a similar mechanism of action for biological activity.
authors.affiliation: Dipartimento di Chimica, Università di Pavia, Via Taramelli 12, 27100 Pavia, Italy.
authors.forename: Alessio
authors.initials: A
authors.lastname: Porta
authors.forename: Maurizio
authors.initials: M
authors.lastname: Pasi
authors.forename: Enrico
authors.initials: E
authors.lastname: Brunoldi
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Zanoni
authors.forename: Giovanni
authors.initials: G
authors.lastname: Vidari
mesh_terms: D003517:Cyclopentanes / Q000737:chemistry*; D004281:Docosahexaenoic Acids / Q000737:chemistry; D005978:Glutathione / Q000737:chemistry; D058632:Neuroprostanes / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D018384:Oxidative Stress; D011453:Prostaglandins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C587329:14-A4-NeuroP; C587328:17-A4-NeuroP; D003517:Cyclopentanes; D058632:Neuroprostanes; D011453:Prostaglandins; D004281:Docosahexaenoic Acids; D005978:Glutathione; C013905:cyclopentenone
keywords: 17-A(4)-NeuroP; A(4)-Neuroprostanes; Docosahexaenoic acid (DHA); Oxidative stress; Total synthesis