Alamethicin
Oxford Dictionary of Biochemistry:
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alamethicin
a linear ionophorous antibiotic polypeptide containing a high proportion of 2-methylalanine residues and blocked at both ends. See also peptaibophols.
Ac-2-MeAla-l-Pro-2-MeAla-l-Ala-2-MeAla-l-Ala-l-Gln-2-MeAla-l-Val-2-MeAla-Gly-l-Leu-2-MeAla-l-Pro-lVal-2-MeAla-2-MeAla-l-Glu-l-Gln-l-phenylalaninol
| al+, akaryotic, ajmaline | |
| alaninal, alaninate, alanine |
Wikipedia on Answers.com:
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Alamethicin
| Alamethicin[1] | |
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N-acetyl-2-methylalanyl-L-prolyl-2-methylalanyl-L-alanyl-2-methylalanyl-L-alanyl-L-glutaminyl-2-methylalanyl-L-valyl-2-methylalanylglycyl-D-leucyl-2-methylalanyl-L-prolyl-L-valyl-2-methylalanyl-2-methylalanyl-L-α-glutamyl-N1-[(1S)-1-benzyl-2-hydroxyethyl]-L-glutamamide |
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| Identifiers | |
| CAS number | 27061-78-5 |
| PubChem | 16132042 |
| ChemSpider | 17288702  |
| ChEMBL | CHEMBL438243 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C92H150N22O25 |
| Molar mass | 1964.31 g/mol |
| Appearance | Off white solid |
| Melting point |
255-270 °C |
| Solubility in water | Insoluble |
| Solubility in DMSO, methanol, ethanol | Soluble |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Alamethicin is a peptide antibiotic, produced by the fungus Trichoderma viride. It contains the non-proteinogenic amino acid 2-aminoisobutyric acid (Aib), which strongly induces helical peptide structures. The peptide sequence is:
Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu-Gln-Phl
(Ac = acetyl, Phl = phenylalaninol)
In cell membranes, it forms voltage-dependent ion channels by aggregation of four to six molecules.
References
Further reading
- LR Jones, SW Maddock and HR Besch Jr. Unmasking effect of alamethicin on the (Na+,K+)-ATPase, beta-adrenergic receptor-coupled adenylate cyclase, and cAMP-dependent protein kinase activities of cardiac sarcolemmal vesicles. J. Biol. Chem., Vol. 255, Issue 20, 9971-9980, Oct, 1980.
- Explore structures of Alamethicin at the protein data bank
- Alamethicin in Norine
- From "A voltage-gated ion channel model inferred from the crystal structure of alamethicin at 1.5-A resolution." Fox Jr, RO; Richards, FM (1982). "A voltage-gated ion channel model inferred from the crystal structure of alamethicin at 1.5-A resolution". Nature 300 (5890): 325–30. Bibcode 1982Natur.300..325F. doi:10.1038/300325a0. PMID 6292726.
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Oxford Dictionary of Biochemistry
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