Pressinoic acid

Base Information

• Chemical Name: Pressinoic acid
• CAS No.: 35748-51-7
• Molecular Formula: C33H42 N8 O10 S2
• Molecular Weight: 774.86
• DSSTox Substance ID: DTXSID80957149
• Mol file: 35748-51-7.mol

Synonyms:L-cysteinyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-cysteine-cyclic (1-6)-disulfide;pressinoic acid

Chemical Property of Pressinoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1373°Cat760mmHg
• Flash Point: 784.2°C
• PSA: 385.26000
• Density: 1.325g/cm³
• LogP: 1.92840
• XLogP3: -4.4
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 10
• Exact Mass: 774.24653191
• Heavy Atom Count: 53
• Complexity: 1330

Purity/Quality:

99% ^*data from raw suppliers

Pressinoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSS1)C(=O)O)CC(=O)N)CCC(=O)N)CC2=CC=CC=C2)CC3=CC=C(C=C3)O)N
• Isomeric SMILES: C1[C@@H](C(=O)N[C@H](C(=O)NC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSS1)C(=O)O)CC(=O)N)CCC(=O)N)CC2=CC=CC=C2)CC3=CC=C(C=C3)O)N

Technology Process of Pressinoic acid

There total 14 articles about Pressinoic acid 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: 100.0%

pressinoic acid (dithiol) (106897-47-6) → pressinoic acid (disulfide) (35748-51-7)

Guidance literature:

With [Pt(en)2Cl₂]⁽²⁺⁾; ethylenediaminetetraacetic acid; sodium chloride; In phosphate buffer; pH=7.3;

DOI:10.1021/ja0008618

Reference yield:

S-benzyl-N-[(benzyloxy)carbonyl]cysteinyltyrosine (39621-64-2) → pressinoic acid (disulfide) (35748-51-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / CaCl₂, thermolysin / dimethylformamide; various solvent(s) / 24 h / 38 °C / pH 7.0

2: 74 percent / 1 M NaOH / dioxane / 3 h / Ambient temperature

3: 64 percent / α-chymotrypsin / dimethylformamide; various solvent(s) / 20 h / 38 °C / pH 7

4: 59 percent / ferric chloride / dimethylformamide; H₂O / 0.5 h / 35 °C

5: 1.) Na/NH₃, 2.) NH₄Cl, 3.) trifluoroacetic acid, O₂

With sodium hydroxide; ammonia; oxygen; sodium; iron(III) chloride; ammonium chloride; trifluoroacetic acid; calcium chloride; α-chymotrypsin; thermolysin; In 1,4-dioxane; water; N,N-dimethyl-formamide;

Reference yield:

phenylalanine phenylhydrazide trifluoroacetate → pressinoic acid (disulfide) (35748-51-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / CaCl₂, thermolysin / dimethylformamide; various solvent(s) / 6 h / 38 °C / pH 7.0

2: 62 percent / ferric chloride / dioxane; H₂O / 0.5 h / 35 °C

3: 64 percent / α-chymotrypsin / dimethylformamide; various solvent(s) / 20 h / 38 °C / pH 7

4: 59 percent / ferric chloride / dimethylformamide; H₂O / 0.5 h / 35 °C

5: 1.) Na/NH₃, 2.) NH₄Cl, 3.) trifluoroacetic acid, O₂

With ammonia; oxygen; sodium; iron(III) chloride; ammonium chloride; trifluoroacetic acid; calcium chloride; α-chymotrypsin; thermolysin; In 1,4-dioxane; water; N,N-dimethyl-formamide;

upstream raw materials:

Benzyloxycarbonyl-S-benzylcysteinyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteine

pressinoic acid (dithiol)

S-benzyl-N-[(benzyloxy)carbonyl]cysteinyltyrosine

benzyloxycarbonyl-S-benzylcysteinyl-tyrosine ethyl ester

Downstream raw materials:

pressinoic acid (dithiol)

Refernces

• 1、 Shi, Tiesheng,Rabenstein, Dallas L.. "Discovery of a highly selective and efficient reagent for formation of intramolecular disulfide bonds in peptides". . p. 6809 - 6815. Retrieved 2007/10/03.