| 词条 | E-64 |
| 释义 |
| Watchedfields = changed | verifiedrevid = 445994617 | ImageFile1=E-64spheres.png | ImageSize1= | ImageFile2=E 64.png | ImageSize2= | IUPACName=(1S,2S)-2-(((S)-1-((4-Guanidinobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)cyclopropanecarboxylic acid | OtherNames=E 64; Proteinase Inhibitor E 64; N-[N-(L-3-trans-carboxyirane-2-carbonyl)-L-leucyl]-agmatine; [1-[N-[(L-3-trans-carboxyoxirane-2-carbonyl)-L-leucyl]amino]-4-guanidinobutane] |Section1= {{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo=66701-25-5 | PubChem = 123985 | ChemSpiderID = 110504 | ChEBI = 30270 | ChEMBL = 374508 | KEGG = C01341 | SMILES=OC([C@@H]1[C@@H](C(N[C@@H](CC(C)C)C(NCCCCNC(N)=N)=O)=O)O1)=O | InChI = 1/C15H27N5O5/c1-8(2)7-9(20-13(22)10-11(25-10)14(23)24)12(21)18-5-3-4-6-19-15(16)17/h8-11H,3-7H2,1-2H3,(H,18,21)(H,20,22)(H,23,24)(H4,16,17,19)/t9-,10-,11-/m0/s1 | InChIKey = LTLYEAJONXGNFG-DCAQKATOBY | StdInChI = 1S/C15H27N5O5/c1-8(2)7-9(20-13(22)10-11(25-10)14(23)24)12(21)18-5-3-4-6-19-15(16)17/h8-11H,3-7H2,1-2H3,(H,18,21)(H,20,22)(H,23,24)(H4,16,17,19)/t9-,10-,11-/m0/s1 | StdInChIKey = LTLYEAJONXGNFG-DCAQKATOSA-N | UNII = R76F7856MV |Section2= {{Chembox Properties | C=15|H=27|N=5|O=5 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3= {{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt= }} E-64 is an epoxide which can irreversibly inhibit a wide range of cysteine peptidases. The compound was first isolated and identified from Aspergillus japonicus in 1978.[1] It has since been shown to inhibit many cysteine peptidases such as papain, cathepsin B, cathepsin L, calpain and staphopain.[2] The low toxic effects of the inhibitor, in addition to its effective mechanism of action, makes E-64 a potential template for drugs to treat diseases where high levels of a cysteine proteases are the primary cause. Structure and mechanism of inhibitionE-64 possesses a trans-epoxysuccinic acid group coupled to a modified dipeptide. The covalent attachment of E-64 to the active site cysteine occurs via nucleophillic attack from the thiol group of the cysteine on C2 of the epoxide. Early studies suggested that the amino-4-guanidinobutane bound in the S3' subsite and the leucyl group in the S2' subsite,[3] however published crystal structures of E-64 complexed with papain and actinidum indicated that E-64 binds via the S subsites.[2] {{clear left}}References1. ^{{cite journal |vauthors=Hanada K, Tamai M, Yamagishi M, Ohmura S, Sawada J, Tanaka I |title= Isolation and Characterization of E–64, a New Thiol Protease Inhibitor|journal=Agric. Biol. Chem. |volume=42 |issue= |pages=523–528|year=1978 |pmid= |doi=10.1080/00021369.1978.10863014}} 2. ^1 {{cite journal |vauthors=Varughese K, Ahmed F, Carey P, Hasnain S, Huber C, Storer A |title=Crystal structure of a papain-E-64 complex |journal=Biochemistry |volume=28 |issue=3 |pages=1332-2|year=1989 |pmid=2713367 |doi=10.1021/bi00429a058}} 3. ^{{cite journal |vauthors=Barrett A, Kembhavi A, Brown M, Kirschke H, Knight C, Tamai M, Hanada K |title=L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L. |journal=J. Biochem. |volume=201 |issue=1 |pages=189–98|year=1982 |pmid=7044372 |doi= 10.1042/bj2010189|pmc=1163625}} 3 : Epoxides|Guanidines|Protease inhibitors |
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