trans-4-Hydroxy-L-proline, ≥99%

• CAS: 51-35-4
• Catalog Number: ACM51354-4
• Category: Amino Acids
• Molecular Weight: 131.13
• Description: Trans-4-hydroxy-L-proline is an isomer of hydroxyproline used as a chiral building block in the production of many pharmaceuticals like neuroexcitatory kainoids.
• Synonyms: (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp
• SMILES: 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
• Melting Point: 273 ℃(dec.) (lit.)
• Application: Versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins. Also employed in the synthesis of chiral ligands for enantioselective ethylation of aldehydes.
• Assay: ≥99%
• Beilstein: 81441
• Biochemical Physiological Action: 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.
• Color: white to off-white
• EC Number: 200-091-9
• Form: crystalline powder
• Impurity Content: ≤0.3% foreign amino acids
• MDL Number: MFCD00064320
• NACRES: NA.22
• Optical Activity: [α]25/D -75.6°, c = 1 in H2O
• PubChem ID: 24895692
• Quality Level: 200
• Reaction Suitability: reaction type: solution phase peptide synthesis
• Storage Temperature: 2-8℃

Synthetic Use

Upstream Synthesis Route 1

• 618-28-0

• 3398-22-9
• 51-35-4

Reference: [1] Chemistry of Materials, 2011, vol. 23, # 5, p. 1280 - 1287

Downstream Synthesis Route 1

• 51-35-4

• 13500-53-3

Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 5004 - 5007

Downstream Synthesis Route 2

• 51-35-4

• 2584-71-6

Reference: [1] Tetrahedron Asymmetry, 2003, vol. 14, # 20, p. 3141 - 3152

Downstream Synthesis Route 3

• 501-53-1
• 51-35-4

• 13504-85-3

Reference: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1845 - 1847

Downstream Synthesis Route 4

• 51-35-4
• 4457-32-3

• 96034-57-0

Reference: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 95 - 99

Downstream Synthesis Route 5

• 27151-65-1
• 108-24-7
• 51-35-4

• 79562-55-3

Reference: [1]Journal of Organic Chemistry,1984,vol. 49,p. 5164 - 5174

* For details of the synthesis route, please refer to the original source to ensure accuracy.