Synthesis of (±)-Cylindricines A, D, and E

Snider, Barry B.; Liu, Tao

doi:10.1021/jo970536b

Cited by 61 publications

(36 citation statements)

References 15 publications

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“…CL provides an anionic platform for electrostatic interaction with the highly cationic cyt c (9 + net charge) so that it is loosely attached to the ETC. The electrostatic interaction of cyt c with CL is supported by high levels of ATP under normal physiological conditions (Sinibaldi et al, 2011;Snider et al, 2013). However, when ATP concentration decreases in pathological conditions such as ischaemia, cyt c becomes tightly associated with CL via hydrophobic interactions.…”

Section: Introductionmentioning

confidence: 99%

Targeting mitochondrial cardiolipin and the cytochrome c/cardiolipin complex to promote electron transport and optimize mitochondrial ATP synthesis

Birk

Chao

Bracken

et al. 2014

British J Pharmacology

259

252

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BACKGROUND AND PURPOSECardiolipin plays an important role in mitochondrial respiration and cardiolipin peroxidation is associated with age-related diseases. Hydrophobic interactions between cytochrome c and cardiolipin converts cytochrome c from an electron carrier to a peroxidase. In addition to cardiolipin peroxidation, this impedes electron flux and inhibits mitochondrial ATP synthesis. SS-31 (D-Arg-dimethylTyr-Lys-Phe-NH2) selectively binds to cardiolipin and inhibits cytochrome c peroxidase activity. Here, we examined whether SS-31 also protected the electron carrier function of cytochrome c. EXPERIMENTAL APPROACHInteractions of SS-31 with cardiolipin were studied using liposomes and bicelles containing phosphatidylcholine alone or with cardiolipin. Structural interactions were assessed by fluorescence spectroscopy, turbidity and nuclear magnetic resonance. Effects of cardiolipin on electron transfer kinetics of cytochrome c were determined by cytochrome c reduction in vitro and oxygen consumption using mitoplasts, frozen and fresh mitochondria.

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Section: Introductionmentioning

confidence: 99%

Targeting mitochondrial cardiolipin and the cytochrome c/cardiolipin complex to promote electron transport and optimize mitochondrial ATP synthesis

Birk

Chao

Bracken

et al. 2014

British J Pharmacology

259

252

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“…Furthermore, aldehyde 43 could also be converted into alkene 46, thus constituting a formal synthesis of cylindricine A. 28 4 Osmium-catalyzed oxidative cyclization for the synthesis of tetrahydrofurans and pyrrolidines…”

Section: Nucleophilic Addition To Pyridinium Saltsmentioning

confidence: 99%

Natural product synthesis as a challenging test of newly developed methodology

Donohoe

Pullin

2012

Chem. Commun.

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“…The first total synthesis of a cylindricine alkaloid was reported by Snider and Liu in 1997. 61 The key steps included in this approach are: a double Michael reaction of ammonia on a dienone 167, obtained from 165 via a Grignard and dehydration reaction to afford 166, to form the fused A/B-ring system and a copper-catalyzed N-chloroamine/olefin radical cyclization for the C-ring construction (Scheme 39).…”

Section: Application Of Aza-michael Addition In Natural Product Synthmentioning

confidence: 99%