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SMB01324

Sigma-Aldrich

Cyclo(His-Pro)

Synonym(s):

Cyclo(L-histidyl-L-proline), Cyclo(histidyl-proline), Cyclo(prolylhistidine), Histidylproline diketopiperazine, Histidylproline dioxopiperazine, CHP

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About This Item

Empirical Formula (Hill Notation):
C11H14N4O2
CAS Number:
53109-32-3
Molecular Weight:
234.25
MDL number:
MFCD00133207
UNSPSC Code:
12352209
NACRES:
NA.26

Assay

98% (HPLC)

Quality Level

100

form

solid

color

white to off-white

mp

162—164 °C

shipped in

2-8°C

storage temp.

−20°C

SMILES string

O=C1N[C@@H](Cc2cnc[nH]2)C(=O)N3CCC[C@@H]13

InChI

1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)/t8-,9-/m0/s1

InChI key

NAKUGCPAQTUSBE-IUCAKERBSA-N

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General description

Cyclo(His-Pro) is a cyclic dipeptide consisting of the amino acids histidine (His) and proline (Pro). This small peptide forms a closed loop, with histidine and proline connected through a peptide bond. It can be found naturally in certain proteins and peptides and can also be synthesized chemically. This unique molecule is related to thyrotropin-releasing hormone and has various roles in the central nervous system. It serves as a substrate for organic cation transporters, making it essential for neuroprotection. Cyclo(His-Pro) holds promise for therapeutic applications, with the potential to counteract neuroinflammation-based degenerative conditions through both oral and parenteral administration routes. It can inhibit NF-κB nuclear accumulation and influence a range of inflammatory and stress responses, making it a valuable asset in the study of cell biology, biochemical research, and neuroprotection research.

Application

Cyclo(L-His-L-Pro) is a versatile molecule and it finds application in biochemical and metabolomics research.

Features and Benefits

  • Can be used in Metabolomics and Biochemical research
  • High-quality compound suitable for multiple research applications

Other Notes

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WGK

WGK 3

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Antagonism of ethanol narcosis by histidyl-proline diketopiperazine.
C Prasad et al.
Nature, 268(5616), 142-144 (1977-07-14)
Silvia Grottelli et al.
Current protein & peptide science, 19(8), 805-812 (2018-05-01)
Protein function is dependent on assumption of the correct three-dimensional structure, achieved through the folding process. As a central element in ensuring cellular homeostasis, proteostasis i.e. the control of correct protein folding, trafficking and degradation, is a highly regulated process
Inhibition of prolactin secretion by histidyl-proline-diketopiperazine.
K Bauer et al.
Nature, 274(5667), 174-175 (1978-07-13)

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