(2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid

• ChemBase ID: 69681
• Molecular Formular: C5H9NO3
• Molecular Mass: 131.12986
• Monoisotopic Mass: 131.05824315
• SMILES: C(=O)([C@@H]1NC[C@@H](C1)O)O
• Canonical SMILES: O[C@H]1CN[C@H](C1)C(=O)O
• InChI: 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
• InChIKey: PMMYEEVYMWASQN-QWWZWVQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid
• IUPAC Traditional name: cis-4-hydroxy-D-proline
• Synonyms: (2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid; D-allo-Hydroxyproline; cis-4-Hydroxy-D-proline; cis-(-)-4-Hydroxy-L-proline; (2S,4S)-(-)-4-Hydroxypyrrolidine-2-carboxylic acid; cis-4-Hydroxy-D-proline; (2R,4R)-(+)-4-Hydroxypyrrolidine-2-carboxylic acid; H-D-cis-Hyp-OH; 顺-4-羟基-D-脯氨酸

Database IDs

• CAS Number: 2584-71-6; 618-27-9
• EC Number: 219-963-5
• MDL Number: MFCD00005252
• Beilstein Number: 81439
• PubChem SID: 24895713; 162035407
• PubChem CID: 440014

CALCULATED PROPERTIES

• Acid pKa: 1.641382
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.7163465
• LogD (pH = 7.4): -3.7165344
• Log P: -3.7163188
• Molar Refractivity: 29.3822 cm^3
• Polarizability: 11.9828205 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 243 °C (dec.)(lit.); 243°C dec.; 257°C
• Optical Rotation: [α]20/D +60±1°, c = 1% in H2O

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (NT); 95+%; 98+%
• Empirical Formula (Hill Notation): C5H9NO3

DETAILS

Sigma Aldrich - H5877

Packaging
1, 10 g in poly bottle
250 mg in poly bottle
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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H5877.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 56246

Biochem/physiol Actions
Cis-4-hydroxy-D-proline is a pharmaceutically active, anti-convulsive, amino acid transported by the proton coupled amino acid transporter (PAT1) expressed in intestine and brain. Cis-4-hydroxy-D-proline upregulates the expression of the hydroxyproline transporter hypM in legume endosymbiont Sinorhizobium meliloti.