H1637

cis-4-Hydroxy-L-proline

collagen synthesis inhibitor

• Synonym(s): (2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid, CHP
• Empirical Formula (Hill Notation): C₅H₉NO₃
• CAS Number: 618-27-9
• Molecular Weight: 131.13
• NACRES: NA.26
• PubChem Substance ID: 24895470
• eCl@ss: 32160406
• UNSPSC Code: 12352209
• EC Number: 210-542-1
• MDL number: MFCD00064319
• Beilstein/REAXYS Number: 81440

Properties

• Quality Segment: 100
• assay: ≥98% (TLC)
• form: powder
• technique(s): ligand binding assay: suitable
• color: white to faint yellow
• mp: 257 °C (dec.) (lit.)
• application(s): peptide synthesis
• SMILES string: O[C@@H]1CN[C@@H](C1)C(O)=O
• InChI: 1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
• InChI key: PMMYEEVYMWASQN-IMJSIDKUSA-N

Description

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.

Other Notes

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)