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H1637 Sigma

cis-4-Hydroxy-L-proline

collagen synthesis inhibitor

Synonym: (2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid, CHP

  • CAS Number 618-27-9

  • Empirical Formula (Hill Notation) C5H9NO3

  • Molecular Weight 131.13

  •  Beilstein Registry Number 81440

  •  EC Number 210-542-1

  •  MDL number MFCD00064319

  •  PubChem Substance ID 24895470

  •  eCl@ss 32160406

  • Popular Documents:  FTNMR (PDF)  

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Description

Other Notes

Constituent of Amanita sp. peptide toxins but not of animal proteins like collagen.

Application

cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line and rat pancreatic carcinoma cell line DSL6A.

Biochem/physiol Actions

cis-4-Hydroxy-L-proline (CHP) and its derivatives may have anticancer activity. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs.

Price and Availability

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Proline Derivatives

Proline is a non-polar, natural amino acid that forms a tertiary amide when incorporated into peptides. Thus, it is the only proteinogenic amino acid that does not act as a hydrogen bond donor in a p...
Matthias Junkers
Aldrich ChemFiles 2008, 8.7, 8.
Keywords: Asymmetric synthesis, Chemfiles, Pharmaceutical

Peer-Reviewed Papers
15

References

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