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
• Beilstein/REAXYS Number: 81440
• EC Number: 210-542-1
• MDL number: MFCD00064319
• UNSPSC Code: 12352209
• eCl@ss: 32160406
• PubChem Substance ID: 24895470
• NACRES: NA.26

Properties

• 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.[1] CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells.[2] CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line[3] and rat pancreatic carcinoma cell line DSL6A.[4]

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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)