1976
DOI: 10.1021/bi00656a012
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Isobongkrekic acid, a new inhibitor of mitochondrial ADP-ATP transport: radioactive labeling and chemical and biological properties

Abstract: An isomer of bongkrekic acid, designated as isobongkrekic acid, has been isolated from ethereal extracts of Pseudomonas cocovenenans grown on defatted coconut. Isobongkrekic acid was also obtained by alkaline treatment of bongkrekic acid. Isobongkrekic acid possesses the same ultraviolet spectrum and the same molecular weight as bongkrekic acid; it has a similar infrared spectrum but not the same nuclear magnetic resonance (NMR) spectrum. The differences in NMR data were interpreted to mean that isobongkrekic … Show more

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Cited by 39 publications
(20 citation statements)
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“…In contrast, BKA, and the related isobongkrekic acid [14], bind to the matrix conformation [11,15]. These observations gave rise to the "single binding centre gated pore mechanism" [15,16], which in essence is an alternating access mechanism, as first proposed for the P--type ATPase [17].…”
Section: Introductionmentioning
confidence: 94%
“…In contrast, BKA, and the related isobongkrekic acid [14], bind to the matrix conformation [11,15]. These observations gave rise to the "single binding centre gated pore mechanism" [15,16], which in essence is an alternating access mechanism, as first proposed for the P--type ATPase [17].…”
Section: Introductionmentioning
confidence: 94%
“…Isobongkrekic acid was prepared as in [17], and [14C]acetylcarboxyatractytoside as in [18], except that the purification procedure by TLC chromatography and DEAE-cellulose was replaced by a reverse-phase highpressure liquid chromatography on a Waters apparat us equipped with a C ls-microbondapack colmnn, with the mobile phase made of water, methanol, acetic acid and 1 M ammonium acetate (60/40/1/2, by vol.). Atractyloside was purchased from Sigma and ADP from PL Biochemicals.…”
Section: Methodsmentioning
confidence: 99%
“…The ratio of 10 for the affinities in both isomers may infact be a low value. Lauquin et al [23] estimated smaller differences (KvKA/K:KA = 4) without a quantitative evaluation.…”
Section: Isohongltrrkurementioning
confidence: 98%
“…Isobongkrekate is a highly welcome and unexpected byproduct of the 3H-labeling of bongkrekate [14,23]. It was identified by us [I 41 by NMR studies and independently by Lauquin et al by mass spectrometry.…”
Section: Isohongltrrkurementioning
confidence: 99%