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C2374

Sigma-Aldrich

Cyclo-Gly-Pro

≥98% (GC/HPLC)

Synonym(s):

(S)-3,6-Dioxohexahydropyrrolo[1,2-a]pyrazine, Glycyl-L-proline lactam, cyclo-GP, cyclo-Glycyl-L-Proline, cyclo-L-prolylglycine

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About This Item

Empirical Formula (Hill Notation):
C7H10N2O2
CAS Number:
3705-27-9
Molecular Weight:
154.17
MDL number:
MFCD01083707
UNSPSC Code:
12352200
PubChem Substance ID:
329774997
NACRES:
NA.32

Assay

≥98% (GC/HPLC)

form

powder

solubility

DMSO: >10 mg/mL

storage temp.

−20°C

SMILES string

O=C1CNC(=O)C2CCCN12

InChI

1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)

InChI key

OWOHLURDBZHNGG-UHFFFAOYSA-N

Biochem/physiol Actions

Cyclo-Gly-Pro is a neuro-protective compound, an endogenous diketopiperazine, which enhances memory. In the animal model of PD, the compound improved functional recovery when administered after the onset of dyskinesia. It appears that the compound recovery function may result from non-proliferative neurogenesis that results from the inhibition of apoptosis of stem cells and/or the promotion of neuronal-orientated proliferation in the SVZ (subventricular zone).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J Guan et al.
Neuropharmacology, 53(6), 749-762 (2007-10-02)
The current study describes the neuroprotective effects of an endogenous diketopiperazine, cyclo-glycyl-proline (cyclic GP), in rats with hypoxic-ischemic brain injury and the pre-clinical development of an analogue, cyclo-L-glycyl-L-2-allylproline (NNZ 2591), modified for improved bioavailability. The compounds were given either intracerebroventricularly
Douglas R Houston et al.
Journal of medicinal chemistry, 47(23), 5713-5720 (2004-10-29)
Family 18 chitinases play an essential role in a range of pathogens and pests. Several inhibitors are known, including the potent inhibitors argadin and allosamidin, and the structures of these in complex with chitinases have been elucidated. Recent structural analysis
J Tritt-Goc et al.
International journal of peptide and protein research, 34(4), 299-305 (1989-10-01)
The complexation of cyclo(Pro17O-Gly15N) and cyclo(Gly17O-Pro) with Co2+ ions has been studied by 17O, 14N and 15N n.m.r. spectroscopy in aqueous solution. 17O, 14N and 15N transverse relaxation times and chemical shifts were measured as a function of temperature. The
F Sussman et al.
Proceedings of the National Academy of Sciences of the United States of America, 86(20), 7880-7884 (1989-10-01)
Calcium plays a crucial role in many cellular processes. Its functions are directly dependent on the high specificity for Ca2+ exhibited by the proteins and ion carriers that bind divalent ions. To elucidate the basis for this specificity we have
Z-F Wu et al.
Scandinavian journal of immunology, 76(2), 131-140 (2012-05-23)
This study was undertaken to isolate active secondary metabolites from immunostimulatory Alcaligenes faecalis FY-3 and evaluate their activities using grass carp Ctenopharyngodon idella kidney (CIK) cells. By applying chromatography techniques and successive recrystallization, three purified metabolites were obtained and identified

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