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

• ChemBase ID: 91182
• Molecular Formular: C5H9NO3
• Molecular Mass: 131.12986
• Monoisotopic Mass: 131.05824315
• SMILES: N1C[C@@H](C[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+/m1/s1
• InChIKey: PMMYEEVYMWASQN-DMTCNVIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
• IUPAC Traditional name: hydroxyproline; hypro
• Synonyms: trans-4-Hydroxy-L-proline; (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid; (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid; L-HYDROXYPROLINE; Hyp; trans-4-Hydroxy-L-proline; cis-4-Hydroxy-D-proline; D-4-allo-Hydroxy-proline; (2R,4R)-4-Hydroxypyrrolidine-2-carboxylic Acid; (4R)-4-Hydroxy-D-proline; (R)-allo-Hydroxyproline; 4-(R)-Hydroxypyrrolidine-2-(R)-carboxylic Acid; 4-Hydroxy-D-alloproline; 4-allo-Hydroxy-D-proline; D-allo-4-Hydroxyproline; D-allo-Hydroxyproline; D-cis-4-Hydroxyproline; NSC 524341; cis-4-Hydroxy-D-proline; (-)-4-Hydroxy-2-pyrrolidinecarboxylic Acid; (2S,4R)-(-)-4-Hydroxyproline; (R)-4-Hydroxy-(S)-proline; 4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic Acid; 4-trans-Hydroxy-L-proline; L-Hypro; NSC 46704; trans-4-Hydroxy-L-proline; trans-4-Hydroxy-D-proline; (2S,4R)-(-)-4-Hydroxypyrrolidine-2-carboxylic acid; H-Hyp-OH; 4-Hydroxyproline; Hydroxyproline; (2S,4R)-4-羟基吡咯烷-2-羧酸; L-羟基脯氨酸; 反-4-羟基-L-脯氨酸

Database IDs

• CAS Number: 147028-80-6; 51-35-4; 2584-71-6; 3398-22-9
• EC Number: 200-091-9
• MDL Number: MFCD00064320
• Beilstein Number: 471933; 81441
• Merck Index: 144840
• PubChem SID: 24895700; 162077886; 24895692; 24880041
• PubChem CID: 5810

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: H2O: soluble50 mg/mL; Water
• Apperance: White Solid
• Melting Point: 270-273°C dec.; 273 °C (dec.)(lit.); 273(dec.)°C; 285-287°C (dec.)
• Optical Rotation: [α]20/D -76.0±1.5°, c = 5% in H2O; [α]25/D -75.6°, c = 1 in H2O; -76 (c=4 in water)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Irritant
• RTECS: TW3586500
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.5%; ≥99%; ≥99.0% (NT); 97%; 98%; 99+%
• Suitability: cell culture tested; suitable for cell culture
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤0.3% foreign amino acids; endotoxin, tested
• Cation Traces: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; NH4+: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤100 mg/kg
• Biological Source: microbial
• Loss on Drying: ≤0.1% loss on drying, 110 °C
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C5H9NO3

DETAILS

MP Biomedicals - 05203349

MP Biomedicals Rare Chemical collection

Sigma Aldrich - H5534

Other Notes
动物结构蛋白（如胶原和弹性蛋白）的天然成分。
包装
10 mg in autosmp vl
Biochem/physiol Actions
Hydroxyproline (4-hydroxyproline) is a non-proteinogenic amino acid formed by the post-translational hydroxylation of proline. Hydroxyproline is a major component of collagen, where it serves to stabilize the helical structure. Because hydroxyproline is largely restricted to collagen, the measurement of hydroxylproline levels can be used as an indicator of collagen content. Conditions that increase collagen turnover can elevate serum and urine hydroxyproline levels. Urine and serum hydroxyproline levels can be used as a marker for bone resorption.

Sigma Aldrich - H3656

Other Notes
动物结构蛋白（如胶原和弹性蛋白）的天然成分。

Sigma Aldrich - 56250

Other Notes
Natural constituent of animal structural proteins such as collagen and elastin.
Enzymes and intermediates of hydroxyproline degradation1
Biochem/physiol Actions
Trans-4-Hydroxy-L-proline is used as a starting material in the synthesis of (-)-secrinine; the synthesis of prolinol-based nucleotide analogues with N-phosphonomethyl moiety attached to the nitrogen atom of prolinol ring and in asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001.
Trans-4-Hydroxy-L-proline is used in the organic synthesis of depsilairdin analogues, noncompetitive peptidomimetic inhibitors of multidrug resistance P-glycoprotein and 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analogues.

Sigma Aldrich - H54409

Other Notes
Natural constituent of animal structural proteins such as collagen and elastin.
Packaging
10, 25, 100 g in poly bottle
2.5 g in glass bottle
Application
Versatile reagent for the synthesis of neuroexcitatory kainoids1 and antifungal echinocandins.2 Also employed in the synthesis of chiral ligands for enantioselective ethylation of aldehydes.3

Toronto Research Chemicals - H952376

A natural constituent of animal structural proteins such as collagen and elastin. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hyd

REFERENCES

• Langmaier, F. et al.: Int. J. Cosm. Sci., 24, 273 (2002)
• Lawrence, C., et al.: Biochem. J., 313, 185 (2002)
• Mori, H., et al.: J. Bacteriol.; 179, 5677 (2002)
• Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (2002)
• Chiral precursor for a wide variety of synthetic targets. For discussion of some examples, see: Tetrahedron, 52, 13803 (1996).