59588-86-2 Usage
Uses
Alamethicin is used as a channel-forming ionophore that activates membrane enzymes, membrane channel-forming peptide. It is a 20-amino acid channel-forming peptide antibiotic that can function as a monovalent cation ionophore. Alamethicin has been used to develop methods for the routine assessment of potential new drug candidates to elicit their pharmacokinetic drug interactions.
Enzyme inhibitor
These voltage-dependent, channel-forming, peptaibol antibiotics
(MWAlamethicin F-30 = 1964.40; CAS 27061-78-5) from the soil fungus
Trichoderma viride NRRL 3199 are membrane-active oligopeptides
isolated from that exhibit anti-bacterial and anti-fungal properties.
Peptaibols are amphipathic, usually highly helical in structure, and
typically form voltage dependent ion channels that uncouple oxidative
phosphorylation, often attended by in bacterial and fungal cell death.
Alamethicin F-30 has the sequence Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-
Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu-Gln-Phe-OH; Alamethicin F-
50 has the sequence Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-
Leu-Aib-Pro-Val-Aib Aib-Gln-Gln-Phe-OH; and Alamethicin II has the
sequence Ac-Aib-Pro-Aib-Ala-Aib-Aib-Gln-Aib-Val-Aib-Gly-Leu-Aib-
Pro-Val-Aib-Aib-Glu-Gln-Phe-OH. Note: The name “peptaibol” is derived
from the prefix “pep-“, the central syllable “aib”, and the suffix “-ol” to
designate its peptide structure, the presence of an a-aminoisobutyryl unit,
and the C-terminal alcohol.
Check Digit Verification of cas no
The CAS Registry Mumber 59588-86-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,5,8 and 8 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 59588-86:
(7*5)+(6*9)+(5*5)+(4*8)+(3*8)+(2*8)+(1*6)=192
192 % 10 = 2
So 59588-86-2 is a valid CAS Registry Number.
59588-86-2Relevant articles and documents
Solid-Phase Synthesis of the Peptaibol Alamethicin U-22324 by Using a Double-Linker Strategy
Siow, Andrew,Hung, Kuo-Yuan,Harris, Paul W. R.,Brimble, Margaret A.
, p. 350 - 354 (2017)
The facile Fmoc (Fluorenylmethoxycarbonyl) solid-phase synthesis of the α-helical-channel-forming peptaibol alamethicin U-22324 is described. A late-stage reduction by using a new double-linker method was used to introduce the C-terminal alcohol. Furthermore, we also report the synthesis of an alamethicin analogue with a C-terminal carboxylic acid.
SOLUTION PHASE SYNTHESIS OF ALAMETHICIN I
Nagaraj, R.,Balaram, P.
, p. 1263 - 1270 (2007/10/02)
The total synthesis of alamethicin I by solution phase methods is reported.
