59588-86-2 Usage
Description
Alamethicin, a 20-amino acid channel-forming peptide antibiotic, is a potent membrane-active compound derived from the fungus Trichoderma viride. It possesses the unique ability to function as a monovalent cation ionophore, allowing it to facilitate the transport of specific ions across cell membranes. This characteristic has made alamethicin a subject of interest in various scientific and medical applications.
Uses
Used in Pharmaceutical Research:
Alamethicin is used as a channel-forming ionophore for activating membrane enzymes. Its ability to form channels in biological membranes has made it a valuable tool in the study of ion transport and membrane protein function. This application aids in the development of new drug candidates and the assessment of their pharmacokinetic drug interactions.
Used in Drug Delivery Systems:
Alamethicin's membrane channel-forming properties have been explored for use in drug delivery systems. By creating temporary pores in cell membranes, alamethicin can potentially enhance the uptake of therapeutic agents, improving their bioavailability and efficacy.
Used in Antimicrobial Applications:
As a peptide antibiotic, alamethicin exhibits antimicrobial activity against a range of pathogens, including bacteria and fungi. Its ability to disrupt cell membranes and interfere with essential cellular processes makes it a promising candidate for the development of new antimicrobial agents, particularly in the context of increasing antibiotic resistance.
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.
