cis-4-Hydroxy-D-proline

• CAS: 2584-71-6
• Catalog Number: ACM2584716-1
• Category: Amino Acids
• Molecular Weight: 131.13
• Synonyms: (2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid, D-allo-Hydroxyproline
• Canonical 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-QWWZWVQMSA-N
• Melting Point: 243 ℃(dec.) (lit.)
• Application: Peptide synthesis.
• Assay: ≥98% (TLC)
• Beilstein: 81439
• Biochem Physiol Actions: Cis-4-Hydroxy-D-proline may be used as a starting material for the 13-step synthesis of new conformationally restricted PNA adenine monomer and the synthesis of N-Benzyl pyrrolidinyl sordaricin derivatives. Cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase. Cis-4-Hydroxy-D-proline may be used to analyze the substrate specificity of amino acid transporter PAT1.
• Color: white
• EC Number: 219-963-5
• Form: powder
• MDL Number: MFCD00005252
• NACRES: NA.26
• PubChem ID: 24895713
• Quality Level: 100
• Storage Temperature: 2-8℃
• Technique: ligand binding assay: suitable

Synthetic Use

Upstream Synthesis Route 1

• 51-35-4

• 2584-71-6

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

Upstream Synthesis Route 2

• 132666-67-2

• 2584-71-6

Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 24, p. 3743 - 3746

Upstream Synthesis Route 3

• 51-35-4

• 2584-71-6

Reference: [1]Heindl, Cornelia; Huebner, Harald; Gmeiner, Peter
[Tetrahedron Asymmetry, 2003, vol. 14, # 20, p. 3141 - 3152]

Downstream Synthesis Route 1

• 2584-71-6

• 13500-53-3

Reference: [1] Patent: WO2018/20358, 2018, A1,

Downstream Synthesis Route 2

• 67-56-1
• 2584-71-6

• 114676-59-4

Reference: [1]Patent: WO2004/7444,2004,A2 .Location in patent: Page 135

Downstream Synthesis Route 3

• 75-36-5
• 2584-71-6

• 114676-59-4

Reference: [1]Synthesis,1988,p. 40 - 44

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