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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.

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.



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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