Cyclo(his-pro)

Base Information

• Chemical Name: Cyclo(his-pro)
• CAS No.: 53109-32-3
• Molecular Formula: C₁₁H₁₄N₄O₂
• Molecular Weight: 234.258
• European Community (EC) Number: 610-961-3
• UNII: Q10817UXVT
• DSSTox Substance ID: DTXSID90962567
• Nikkaji Number: J456.134A
• Wikidata: Q27286866
• Metabolomics Workbench ID: 147001
• ChEMBL ID: CHEMBL188225
• Mol file: 53109-32-3.mol

Synonyms:cyclo(His-Pro);cyclo(histidyl-prolyl);His-Pro-Dkp;histidyl-proline diketopiperazine;histidyl-proline diketopiperazine, (3R-cis)-isomer;histidyl-proline diketopiperazine, (3S-cis)-isomer;histidyl-proline diketopiperazine, (3S-trans)-isomer;histidyl-proline-diketopiperazine

Chemical Property of Cyclo(his-pro)

Chemical Property:

• Vapor Pressure: 2.69E-23mmHg at 25°C
• Melting Point: 162-164 °C
• Boiling Point: 650.3°Cat760mmHg
• PKA: 12.73±0.40(Predicted)
• Flash Point: 347.1°C
• PSA: 78.09000
• Density: 1.36g/cm³
• LogP: -0.29170
• Storage Temp.: 2-8°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 234.11167570
• Heavy Atom Count: 17
• Complexity: 346

Purity/Quality:

98%Min ^*data from raw suppliers

Cyclo(his-pro) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(=O)NC(C(=O)N2C1)CC3=CN=CN3
• Isomeric SMILES: C1C[C@H]2C(=O)N[C@H](C(=O)N2C1)CC3=CN=CN3
• Uses: Cyclo(L-histidyl-L-proline) is used in the pharmaceutical composition comprising cyclo(His-Pro) for preventing or treating obesity.

Technology Process of Cyclo(his-pro)

There total 11 articles about Cyclo(his-pro) 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%

L-histidine-L-proline methyl dihydrochloride → cyclo(His-Pro) (53109-32-3)

Guidance literature:

With sodium hydrogencarbonate; In water; at 130 ℃; for 2.5h; under 1275.13 Torr; pH=6; Temperature; Pressure; Sealed tube;

Reference yield: 26.0%

N-(tert-butoxycarbonyl)-L-prolyl-L-histidine methyl ester bis(trifluoroacetate) (97997-80-3) → cyclo(L-histidyl-L-proline) (53109-32-3)

Guidance literature:

With potassium hydrogencarbonate; In methanol; for 144h; Heating;

DOI:10.1021/jm00149a035

Reference yield:

N-benzyloxycarbonyl-L-proline p-nitrophenyl ester (3304-59-4) → cyclo(His-Pro) (53109-32-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CHCl₃ / Ambient temperature

2: H₂ / 10percent Pd/C / ethanol

3: methanol / Heating

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; ethanol; chloroform;

upstream raw materials:

Pro-His-OMe

N-benzyloxycarbonyl-L-proline p-nitrophenyl ester

Benzyloxycarbonyl-Pro-His-OMe

N-Benzyloxycarbonyl-L-proline

Refernces

• 1、 Singh, Palwinder,Singh, Amrinder,Kaur, Sukhmeet,Mithu, Venus Singh,Bhatti, Manpreet S.. "Temperature, pH and H-bond synergism for peptide bond formation: Synthesis of sequence specific tetra- and penta-peptides without using coupling reagent". . p. 37371 - 37374. Retrieved 2014/12/11.
• 2、 Arena, Giuseppe,Impellizzeri, Giuseppe,Maccarrone, Giuseppe,Pappalardo, Giuseppe,Sciotto, Domenico,Rizzarelli, Enrico. "Thermodynamic and (1)H NMR Study of Proton Complex Formation of Histidine-containing Cyclodipeptides in Aqueous Solution". . p. 371 - 376. Retrieved 2007/10/02.