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56250 Sigma

trans-4-Hydroxy-L-proline

BioXtra, ≥99.0% (NT)

Synonym: (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp

  • CAS Number 51-35-4

  • Empirical Formula (Hill Notation) C5H9NO3

  • Molecular Weight 131.13

  •  Beilstein Registry Number 81441

  •  EC Number 200-091-9

  •  MDL number MFCD00064320

  •  PubChem Substance ID 57651574

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Properties

Related Categories A - H, Aloe Vera, Amino Acids, Biochemicals and Reagents, Cell Biology,
InChI Key   PMMYEEVYMWASQN-DMTCNVIQSA-N
product line   BioXtra
assay   ≥99.0% (NT)
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
mp   273 °C (dec.)(lit.)
anion traces   chloride (Cl-): ≤100 mg/kg
  sulfate (SO42-): ≤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

Description

Other Notes

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

Enzymes and intermediates of hydroxyproline degradation

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.

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Laboratory Gloves

All labs need water
Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Proline Derivatives and Analogs

Proline is a non-polar proteinogenic amino acid that forms a tertiary amide when incorporated into peptides. It does not have a hydrogen on the amide group and therefore cannot act as a hydrogen bond...
Chemfiles Volume 5 Article 12
Keywords: Adhesion, Biochemistry, Catalysis, Deposition, Hydroxylations, Isomerizations, Nucleic acid hybridization, Pharmaceutical, Reductions, Substitutions, Type

Peer-Reviewed Papers
15

References

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