Oxiranecarboxylic acid, [2S-[2alpha,3beta(R*)]]-

Base Information

• Chemical Name: Oxiranecarboxylic acid, [2S-[2alpha,3beta(R*)]]-
• CAS No.: 76684-89-4
• Molecular Formula: C15H26 N2 O5
• Molecular Weight: 314.382
• Hs Code.: 29241990
• NSC Number: 694279
• DSSTox Substance ID: DTXSID10997997
• ChEMBL ID: CHEMBL1973415
• Mol file: 76684-89-4.mol

Synonyms:C15H26N2O5;C15-H26-N2-O5;SCHEMBL6041204;CHEMBL1973415;DTXSID10997997;NSC694279;NSC-694279;NCI60_033763;A903413;Oxiranecarboxylic acid, [2S-[2.alpha.,3.beta.(R*)]]-;(2S,3S)-3-(((S)-1-(isopentylaMino)-4-Methyl-1-oxopentan-2-yl)carbaMoyl)oxirane-2-carboxylic acid;Loxistatin acid;3-[Hydroxy({1-hydroxy-4-methyl-1-[(3-methylbutyl)imino]pentan-2-yl}imino)methyl]oxirane-2-carboxylic acid

Chemical Property of Oxiranecarboxylic acid, [2S-[2alpha,3beta(R*)]]-

Chemical Property:

• Vapor Pressure: 9.14E-16mmHg at 25°C
• Boiling Point: 596.4°C at 760 mmHg
• Flash Point: 314.5°C
• PSA: 108.03000
• Density: 1.169g/cm³
• LogP: 1.31340
• Storage Temp.: −20°C
• Solubility.: ≥31.4 mg/mL in DMSO; insoluble in H2O; ≥111.8 mg/mL in EtOH
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 314.18417193
• Heavy Atom Count: 22
• Complexity: 422

Purity/Quality:

99.3% ^*data from raw suppliers

E-64c ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCNC(=O)C(CC(C)C)NC(=O)C1C(O1)C(=O)O
• Isomeric SMILES: CC(C)CCNC(=O)C(CC(C)C)NC(=O)[C@@H]1[C@H](O1)C(=O)O
• Description: E-64c is an active metabolite of the protease inhibitor E-64d . E-64c inhibits the cysteine proteases cathepsin B, cathepsin H, and papain but not the serine proteases trypsin, chymotrypsin, or elastase. It reduces the autocatalytic activity of the foot-and-mouth-disease virus (FMDV) leader protease when used at concentrations ranging from 0.1 to 1 mg/ml. E-64c reduces infection of HEK293T cells by an HIV-based virus system pseudotyped with severe acute respiratory syndrome coronavirus (SARS-CoV) surface glycoprotein, also known as the spike glycoprotein, in a concentration-dependent manner.
• Uses: E-64c is a cysteine protease inhibitor used for detecting autophagy in plants.

Technology Process of Oxiranecarboxylic acid, [2S-[2alpha,3beta(R*)]]-

There total 11 articles about Oxiranecarboxylic acid, [2S-[2alpha,3beta(R*)]]- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

aloxistatin (88321-09-9) → loxistatin acid (76684-89-4)

Guidance literature:

With potassium hydroxide; for 5h; Heating;

DOI:10.1016/j.cclet.2013.05.002

Reference yield: 53.0%

C21H30N2O5 (915697-62-0) → loxistatin acid (76684-89-4)

Guidance literature:

With potassium hydroxide; In ethanol; at 0 ℃; for 0.5h;

DOI:10.1055/s-2006-948191

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → loxistatin acid (76684-89-4)

Guidance literature:

Multi-step reaction with 5 steps

1: N-methylmorpholine / ethyl acetate / 0.33 h

2: N-methylmorpholine / ethyl acetate

3: 100 percent / 4N HCl / dioxane / 0.75 h / Ambient temperature

4: N-methylmorpholine / ethyl acetate

5: 84 percent / 1N NaOH / ethanol / 1 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; In 1,4-dioxane; ethanol; ethyl acetate;

DOI:10.1021/jm950445b

upstream raw materials:

aloxistatin

C₂₁H₃₀N₂O₅

C₂₁H₃₀N₂O₄

C₁₆H₁₉NO₅

Downstream raw materials:

(2S,3S)-3-[(S)-3-Methyl-1-(3-methyl-butylcarbamoyl)-butylcarbamoyl]-oxirane-2-carboxylic acid (S)-2-((S)-2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-hexyl ester

5-<3-<2-ethyl>-1H-indolyl> (+)-(2S,3S)-3-<<(S)-3-methyl-1-<(3-methylbutyl)carbamoyl>butyl>carbamoyl>-2-oxiranecarboxylate

(R)-2-({(2S,3S)-3-[(S)-3-Methyl-1-(3-methyl-butylcarbamoyl)-butylcarbamoyl]-oxiranecarbonyl}-amino)-3-phenyl-propionic acid methyl ester

N-<2-<5-(benzyloxy)-1H-indol-3-yl>ethyl> (2S,3S)-3-<<(S)-3-methyl-1-<(3-methylbutyl)carbamoyl>butyl>carbamoyl>-2-oxiranecarboxamide

Refernces

• 1、 Lygo, Barry,Gardiner, Stuart D.,To, Daniel C. M.. "Stereoselective synthesis of the epoxysuccinyl peptide E-64c". . p. 2063 - 2066. Retrieved 2008/02/05.
• 2、 Huang,McGowan,Detwiler. "Ester and amide derivatives of E64c as inhibitors of platelet calpains". . p. 2048 - 2054. Retrieved 2007/10/02.