Amastatin

Amastatin

Systematic (IUPAC) name
(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-Amino-2-hydroxy-5-methylhexanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]butanedioic acid
Identifiers
CAS Number	67655-94-1
ATC code	None
PubChem	CID: 439518
ChemSpider	388612
Chemical data
Formula	C21H38N4O8
Molecular mass	474.54842 g/mol
SMILES CC(C)CC(C(C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CC(=O)O)C(=O)O)O)N
InChI InChI=1S/C21H38N4O8/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33)/t12-,13+,15+,16+,17+/m1/s1 Key:QFAADIRHLBXJJS-ZAZJUGBXSA-N

Amastatin, also known as 3-amino-2-hydroxy-5-methylhexanoyl-L-valyl-L-valyl-L-aspartic acid, is a naturally occurring, competitive and reversible aminopeptidase inhibitor that was isolated from Streptomyces sp. ME 98-M3. It specifically inhibits leucyl aminopeptidase, alanyl aminopeptidase (aminopeptidase M/N), bacterial leucyl aminopeptidase (Aeromonas proteolytica aminopeptidase), leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase), and, to a lesser extent, glutamyl aminopeptidase (aminopeptidase A), as well as other aminopeptidases. It does not inhibit arginyl aminopeptidase (aminopeptidase B). Amastatin has been found to potentiate the central nervous system effects of oxytocin and vasopressin in vivo. It also inhibits the degradation of met-enkephalin, dynorphin A, and other endogenous peptides.

See also

• Bestatin
• Pepstatin