(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid

• ChemBase ID: 132377
• Molecular Formular: C5H9NO3
• Molecular Mass: 131.12986
• Monoisotopic Mass: 131.05824315
• SMILES: C1[C@@H](CN[C@@H]1C(=O)O)O
• Canonical SMILES: O[C@@H]1CN[C@@H](C1)C(=O)O
• InChI: 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
• InChIKey: PMMYEEVYMWASQN-IMJSIDKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid
• IUPAC Traditional name: L-hydroxyproline
• Synonyms: CHP; cis-4-Hydroxy-L-proline; (2S,4S)-(-)-4-Hydroxy-2-pyrrolidinecarboxylic acid; (4S)-4-Hydroxy-L-proline; (2S,4S)-4-Hydroxyproline; (S)-Allo-hydroxyproline; (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic Acid; L-Allohydroxyproline; cis-4-Hydroxyproline; cis-Hydroxyproline; cis-4-Hydroxy-L-proline; (2S,4S)-(-)-4-Hydroxypyrrolidine-2-carboxylic acid; H-cis-Hyp-OH; (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid; (2S,4S)-(-)-4-羟基-2-吡咯烷羧酸; 顺式-4-羟基-L-脯氨酸; 顺-4-羟基-L-脯氨酸

Database IDs

• CAS Number: 618-27-9
• EC Number: 210-542-1
• MDL Number: MFCD00064319
• Beilstein Number: 81440
• PubChem SID: 24880039; 162226654; 24895470
• PubChem CID: 440015

CALCULATED PROPERTIES

• Acid pKa: 1.641382
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.7163465
• LogD (pH = 7.4): -3.7165344
• Log P: -3.7163188
• Molar Refractivity: 29.3822 cm^3
• Polarizability: 11.9828205 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: WHite Solid
• Melting Point: <225°C (dec.); 253-257 °C (dec.); 257 °C (dec.)(lit.); ca 250°C dec.
• Optical Rotation: [α]20/D -59.0°, c = 2 in H2O; [α]20/D -59±1°, c = 1% in H2O; -59 (c=2 in water)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (NT); 97%; 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C5H9NO3

DETAILS

Sigma Aldrich - H1637

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.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 line3 and rat pancreatic carcinoma cell line DSL6A.4

Sigma Aldrich - 56248

Other Notes
Proline antagonist in collagen synthesis. Inhibits human skin fibroblast growth and collagen production in culture1; Specifically inhibits cultured tumour cells that synthesize basement-membrane collagen2,3; Its incorporation inhibits secretion of procollagen4

Toronto Research Chemicals - H952375

Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- a

REFERENCES

• Lawrence, C., et al.: Biochem. J., 313, 185 (1996)
• Mori, H., et al.: J. Bacteriol., 179, 5677 (1996)
• Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (1996)