Alamethicin

Alamethicin
IUPAC name 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
Identifiers
CAS number	27061-78-5
PubChem	16132042
ChemSpider	17288702 Y
ChEMBL	CHEMBL438243 Y
Jmol-3D images	Image 1 Image 2
SMILES CC(C)C[C@@H](C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC2=CC=CC=C2)CO)NC(=O)CNC(=O)C(C)(C)NC(=O)[C@H](C(C)C)NC(=O)C(C)(C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]3CCCN3C(=O)C(C)(C)NC(=O)C CC(C)CC(C(=O)NC(C)(C)C(=O)N1CCCC1C(=O)NC(C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)N)C(=O)NC(Cc2ccccc2)CO)NC(=O)CNC(=O)C(C)(C)NC(=O)C(C(C)C)NC(=O)C(C)(C)NC(=O)C(CCC(=O)N)NC(=O)C(C)NC(=O)C(C)(C)NC(=O)C(C)NC(=O)C(C)(C)NC(=O)C3CCCN3C(=O)C(C)(C)NC(=O)C
InChI InChI=1S/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)/t50-,51-,54-,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1 Y Key: LGHSQOCGTJHDIL-UTXLBGCNSA-N Y InChI=1/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)/t50-,51-,54-,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1 Key: LGHSQOCGTJHDIL-UTXLBGCNBC
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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 the crystal structure at the protein data bank: http://www.rcsb.org/pdb/explore/explore.do?pdbId=1AMT
  • 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.