Cyclo(D-Leu-L-Pro)

Base Information

• Chemical Name: Cyclo(D-Leu-L-Pro)
• CAS No.: 36238-67-2
• Molecular Formula: C11H18N2O2
• Molecular Weight: 210.276
• DSSTox Substance ID: DTXSID101157974
• Nikkaji Number: J92.059B
• Wikidata: Q105264164
• ChEMBL ID: CHEMBL463718
• Mol file: 36238-67-2.mol

Synonyms:Cyclo(D-Leu-L-Pro);36238-67-2;Cyclo[D-Leu-L-Pro-];(3R,8aS)-3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(D-Leu-L-Pro-);CHEMBL463718;CHEBI:182342;DTXSID101157974;AKOS040763114;(3R,8aS)-Hexahydro-3-(2-methylpropyl)pyrrolo[1,2-a]pyrazine-1,4-dione;(3R,8aS)-3-isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Chemical Property of Cyclo(D-Leu-L-Pro)

Chemical Property:

• Melting Point: 154-157℃
• PSA: 49.41000
• LogP: 0.78860
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 210.136827821
• Heavy Atom Count: 15
• Complexity: 288

Purity/Quality:

> 95% ^*data from raw suppliers

Cyclo(D-Leu-L-Pro) 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1C(=O)N2CCCC2C(=O)N1
• Isomeric SMILES: CC(C)C[C@@H]1C(=O)N2CCC[C@H]2C(=O)N1
• Uses: Cyclo(D-Leu-L-Pro) is used in the inhibitory effect of three diketopiperazines from marine-derived bacteria on secretory group IIa phospholipase a2.

Technology Process of Cyclo(D-Leu-L-Pro)

There total 22 articles about Cyclo(D-Leu-L-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: 87.0%

cyclo(Z-L-Leu-D-Pro) (1380332-79-5) → (3S,8aR)-3-isobutyl-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (2873-36-1,5654-86-4,19943-30-7,32510-93-3,36238-67-2,43041-29-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 24h;

DOI:10.1002/chem.201103143

Reference yield:

→ pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)- (2873-36-1,5654-86-4,19943-30-7,32510-93-3,36238-67-2,43041-29-8)

Guidance literature:

at 180 ℃; L-leucyl-DL-proline-anhydride; im Vakuum;

Reference yield:

DL-leucine ethyl ester (2899-43-6,75023-21-1) → pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)- (2873-36-1,5654-86-4,19943-30-7,32510-93-3,36238-67-2,43041-29-8)

Guidance literature:

With chloroform; lactam of -l-proline; Entfernen des Chlors aus dem Reaktionsprodukt; Saettigen der alkoh. Loesung mit Ammoniak;

upstream raw materials:

DL-leucine ethyl ester

L-prolyl-L-leucine

L-prolyl-L-leucylglycylglycine

Z-Leu-OH

Downstream raw materials:

L-leucine

L-proline

(8aR)-3c-isobutyl-(8ar)-octahydro-pyrrolo[1,2-a]pyrazine

Refernces

• 1、 Dewan, Faizunnahar,Domzalski, Alison,Kawamura, Akira,Margent, Liliana,Pilarsetty, Naga Vara Kishore,Vigo, Valeria,Xu, Yujia. "Unambiguous stereochemical assignment of cyclo(Phe-pro), cyclo(leu-pro), and cyclo(val-pro) by electronic circular dichroic spectroscopy". . . Retrieved 2021/10/12.
• 2、 Monbaliu, Jean-Christophe M.,Hansen, Finn K.,Beagle, Lucas K.,Panzner, Matthew J.,Steel, Peter J.,Todadze, Ekaterina,Stevens, Christian V.,Katritzky, Alan R.. "A new benzotriazole-mediated stereoflexible gateway to hetero-2,5- diketopiperazines". . p. 2632 - 2638. Retrieved 2012/04/17.