Skip to Content
Merck
All Photos(1)

Key Documents

SMB01324

Sigma-Aldrich

Cyclo(His-Pro)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing

Select a Size


Select a Size

Change View

About This Item

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

Assay

98% (HPLC)

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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

For additional information on our range of Biochemicals, please complete this form.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Antagonism of ethanol narcosis by histidyl-proline diketopiperazine.
C Prasad et al.
Nature, 268(5616), 142-144 (1977-07-14)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service