56250

trans-4-Hydroxy-L-proline

BioXtra, ≥99.0% (NT)

• Synonym(s): (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp
• Empirical Formula (Hill Notation): C₅H₉NO₃
• CAS Number: 51-35-4
• Molecular Weight: 131.13
• Beilstein: 81441
• EC Number: 200-091-9
• MDL number: MFCD00064320
• UNSPSC Code: 12352209
• PubChem Substance ID: 57651574
• NACRES: NA.26

Properties

• product line: BioXtra
• Quality Level: 100
• Assay: ≥99.0% (NT)
• form: solid
• optical activity: [α]20/D −76.0±1.5°, c = 5% in H₂O
• impurities: ≤0.3% foreign amino acids
• ign. residue: ≤0.1% (as SO₄)
• loss: ≤0.1% loss on drying, 110 °C
• color: colorless to white
• mp: 273 °C (dec.) (lit.)
• anion traces: chloride (Cl^-): ≤100 mg/kg; sulfate (SO₄^2-): ≤100 mg/kg
• 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; NH₄⁺: ≤100 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• 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+/m1/s1
• InChI key: PMMYEEVYMWASQN-DMTCNVIQSA-N

Description

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.

Other Notes

Natural constituent of animal structural proteins such as collagen and elastin.

Enzymes and intermediates of hydroxyproline degradation

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves