Calpeptin

Base Information

• Chemical Name: Calpeptin
• CAS No.: 117591-20-5
• Molecular Formula: C20H30 N2 O4
• Molecular Weight: 362.469
• Hs Code.: 29242990
• UNII: 18X9FR245W
• DSSTox Substance ID: DTXSID90922464
• Nikkaji Number: J739.130G
• Wikidata: Q27106026
• Pharos Ligand ID: AWLBKJ8N5RC2
• Metabolomics Workbench ID: 67913
• ChEMBL ID: CHEMBL92708
• Mol file: 117591-20-5.mol

Synonyms:benzylcarbonyl-Leu-nLeu-H;calpeptin;carbamic acid, N-((1S)-1-((((1S)-1-formylpentyl)amino)carbonyl)-3-methylbutyl)-, phenylmethyl ester;N-CBZ-Leu-nLeu-al;SR 914;SR-914;SR914

Chemical Property of Calpeptin

Chemical Property:

• Appearance/Colour: White to off-white powder.
• Vapor Pressure: 3.57E-12mmHg at 25°C
• Melting Point: 60-75 °C
• Refractive Index: 1.6800 (estimate)
• Boiling Point: 550.7 °C at 760 mmHg
• Flash Point: 286.8 °C
• PSA: 84.50000
• Density: 1.075 g/cm³
• LogP: 3.98320
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO at 15mg/ml
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 362.22055744
• Heavy Atom Count: 26
• Complexity: 434

Purity/Quality:

98%,99%, ^*data from raw suppliers

Calpeptin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C=O)NC(=O)C(CC(C)C)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CCCC[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1
• Uses: Calpeptin is used to to inhibit the activities of cathepsin L and calpain-1. Calpeptin blocked the expression of aspartyl protease cathepsin D, amyloid precursor protein, and calparin. It acts as an inhibitor of the Ca2+-dependent protease, calpain. Prevents collagen- and thrombin-induced platelet aggregation, probably by blocking calpain induced phospholipase C and thromboxane synthase activation. Potent cathepsin L inhibitor. It is shown to preferentially inhibit a subset of protein-tyrosine phosphatases.

Technology Process of Calpeptin

There total 4 articles about Calpeptin 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: 78.0%

Z-Leu-nLeu-OH (117611-44-6) → calpeptin (117591-20-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -65 ℃;

DOI:10.1016/j.bmcl.2005.05.091

Reference yield: 78.0%

→ calpeptin (117591-20-5)

Guidance literature:

Reference yield:

Z-Leu-OH (2018-66-8) → calpeptin (117591-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / EDC; HOBT; N-methylmorpholine

2: 78 percent / DMSO; (COCl)2 / CH₂Cl₂ / -65 °C

With 4-methyl-morpholine; oxalyl dichloride; benzotriazol-1-ol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1016/j.bmcl.2005.05.091

upstream raw materials:

Z-Leu-nLeu-OH

Z-Leu-OH

(S)-(+)-2-Amino-1-hexanol

Downstream raw materials:

((S)-1-{(S)-1-[(tert-Butyl-dimethyl-silanyloxy)-thiocarbamoyl-methyl]-pentylcarbamoyl}-3-methyl-butyl)-carbamic acid benzyl ester

2-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-(tert-butyl-dimethyl-silanyloxy)-hexyl]-thiazole-4-carboxylic acid ethyl ester

((S)-1-{(S)-1-[(tert-Butyl-dimethyl-silanyloxy)-cyano-methyl]-pentylcarbamoyl}-3-methyl-butyl)-carbamic acid benzyl ester

Refernces

• 1、 -. "Cycloalkylcarbonylamino Acid Ester Derivative and Process for Producing The Same". Page/Page column 68. . Retrieved 2009/06/27.
• 2、 -. "CYCLOALKANECARBOXAMIDE DERIVATIVE AND METHOD FOR PRODUCING SAME". Page/Page column 96. . Retrieved 2008/12/08.