12689-26-8 Usage
Description
Ilicicolin H is a potent inhibitor of the mitochondrial cytochrome bc1 reductase, which displays broad-spectrum antifungal activity.
Uses
Used in Pharmaceutical Industry:
Ilicicolin H is used as an antifungal agent for its potent and broad-spectrum activity against various fungal infections. Its ability to inhibit the mitochondrial cytochrome bc1 reductase makes it a promising candidate for the development of new antifungal drugs to combat resistant strains and improve treatment outcomes.
References
1) Singh et al. (2013), Structure-activity relationship of cytochrome bc1 reductase inhibitor broad spectrum antifungal ilicicolin H; Bioorg. Med. Chem., 23 3018
2) Singh et al. (2012), Antifungal spectrum, in vivo efficacy, and structure-activity relationship of ilicicolin h; ACS Med. Chem. Lett., 3 814
Check Digit Verification of cas no
The CAS Registry Mumber 12689-26-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,2,6,8 and 9 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 12689-26:
(7*1)+(6*2)+(5*6)+(4*8)+(3*9)+(2*2)+(1*6)=118
118 % 10 = 8
So 12689-26-8 is a valid CAS Registry Number.
12689-26-8Relevant articles and documents
Enzyme-Catalyzed Inverse-Electron Demand Diels-Alder Reaction in the Biosynthesis of Antifungal Ilicicolin H
Zhang, Zhuan,Jamieson, Cooper S.,Zhao, Yi-Lei,Li, Dehai,Ohashi, Masao,Houk,Tang, Yi
supporting information, p. 5659 - 5663 (2019/04/26)
The pericyclases are a growing superfamily of enzymes that catalyze pericyclic reactions. We report a pericyclase IccD catalyzing an inverse-electron demand Diels-Alder (IEDDA) reaction with a rate acceleration of 3 × 105-fold in the biosynthesis of fungal natural product ilicicolin H. We demonstrate IccD is highly periselective toward the IEDDA cycloaddition over a competing normal electron demand Diels-Alder (NEDDA) reaction from an ambimodal transition state. A predicted flavoenzyme IccE was identified to epimerize the IEDDA product 8-epi-ilicicolin H to ilicicolin H, a step that is critical for the observed antifungal activity of ilicicolin H. Our results reveal the ilicicolin H biosynthetic pathway and add to the collection of pericyclic reactions that are catalyzed by pericyclases.