Cyclo(-D-Ala-L-Pro)

• CAT Number: R074523
• CAS Number: 36238-64-9
• PubChem Substance ID: 11902953
• Molecular Formula: C8H12N2O2
• Molecular Weight: 168.196
• Purity: 98%
• Target: Disease Research Fields
• Appearance: White solid
• Analysis method: HPLC
• IUPAC Name: (3R,8aS)-3-methyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• InChI: InChI=1S/C8H12N2O2/c1-5-8(12)10-4-2-3-6(10)7(11)9-5/h5-6H,2-4H2,1H3,(H,9,11)/t5-,6+/m1/s1
• InChIKey: WSLYCILIEOFQPK-RITPCOANSA-N
• SMILES: CC1C(=O)N2CCCC2C(=O)N1

Cyclo(D-Ala-L-Pro) is an unusual D-amino acid-containing diketopiperazine metabolite reported as a fermentation product from
Penicillium terrestre, an endolichenous Colpoma sp. and a marine sponge extract. In all cases, cyclo(D-Ala-L-Pro) was found
co-produced with L-amino acid-containing diketopiperazines. No biological activity has been reported, although cyclo(D-Ala-LPro) appears in several recent patents covering a diverse range of diketopiperazines with broad therapeutic claims.

Reference

1. A new 1,4-diazepine from South China Sea marine sponge Callyspongia species. Huang R-M. et al., Molecules
2010, 15, 871.
2. Secondary metabolites from marine derived fungus Penicillium terrestre. Liu H. et al., J. Chin. Pharm. Sci. 2010,
19, 482.
3. Diketopiperazines from Costa Rican endolichenic fungus Colpoma sp. CR1465A Lee S. et al., Bioorg. Med.
Chem. Lett. 2016, 26, 2438.