Introduction：Basic information about D-Proline CAS 344-25-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
D-Proline Basic information
| Product Name: | D-Proline |
| Synonyms: | D-Pro-OH;D-Proline≥ 99% (Assay);D-Proline,99%e.e.;(R)-(+)-PROLINE;(R)-PYRROLIDINE-2-CARBOXYLIC ACID;D-2-PYRROLIDINECARBOXYLIC ACID;D-PYRROLIDINE-2-CARBOXYLIC ACID;D(+)-PROLINE |
| CAS: | 344-25-2 |
| MF: | C5H9NO2 |
| MW: | 115.13 |
| EINECS: | 206-452-7 |
| Product Categories: | Amino Acids and Derivatives;Proline [Pro, P];Amino Acids and Derivatives;alpha-Amino Acids;Amino Acids;Biochemistry;Amino Acids & Derivatives;Heterocycles;Isotope Labelled Compounds;206-452-7;Amino ACIDS SERIES;Miscellaneous Biochemicals;bc0001 |
| Mol File: | 344-25-2.mol |
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D-Proline Chemical Properties
| Melting point | 223 °C (dec.) (lit.) |
| alpha | 84.75 º (c=4, H2O) |
| Boiling point | 215.41°C (rough estimate) |
| density | 1.36 |
| refractive index | 85 ° (C=4, H2O) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Methanol (Slightly), Water (Sparingly) |
| pka | 1.952(at 25℃) |
| form | Powder |
| color | White to yellow to pale brown |
| Optical Rotation | [α]22/D +85.0°, c = 4 in H2O |
| Water Solubility | soluble >1000 g/L (20 ºC) |
| Sensitive | Hygroscopic |
| BRN | 80811 |
| InChI | 1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1 |
| InChIKey | ONIBWKKTOPOVIA-SCSAIBSYSA-N |
| SMILES | OC(=O)[C@H]1CCCN1 |
| LogP | -0.060 (est) |
| CAS DataBase Reference | 344-25-2(CAS DataBase Reference) |
| EPA Substance Registry System | D-Proline (344-25-2) |
Safety Information
| Hazard Codes | Xi,Xn |
| Risk Statements | 22-36/37/38 |
| Safety Statements | 22-24/25-36/37/39-26 |
| WGK Germany | 3 |
| F | 3-10 |
| Hazard Note | Irritant |
| TSCA | TSCA listed |
| HS Code | 29339990 |
| Storage Class | 11 - Combustible Solids |
D-Proline Usage And Synthesis
| Chemical Properties | White to off-white powder |
| Occurrence | D-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva. These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity. |
| Uses | proline is a skin-conditioning agent. An amino acid found in the collagen molecule. |
| Uses | Used in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C. |
| Uses | Labelled D-ProlineLasubine II and (+)-Cermizine C. |
| Definition | ChEBI: D-proline is the D-enantiomer of proline. It has a role as a mouse metabolite. It is a D-alpha-amino acid and a proline. It is a conjugate base of a D-prolinium. It is a conjugate acid of a D-prolinate. It is an enantiomer of a L-proline. It is a tautomer of a D-proline zwitterion. |
| Synthesis Reference(s) | Journal of the American Chemical Society, 71, p. 2818, 1949 DOI: 10.1021/ja01176a065
Tetrahedron Letters, 28, p. 6469, 1987 DOI: 10.1016/S0040-4039(00)96890-4 |
| reaction suitability | reaction type: solution phase peptide synthesis |
| Synthesis | D-amino acids are an important class of chiral reagents and chiral intermediates. Currently, most of the D-amino acids are produced by synthesizing the racemates and then splitting them to obtain the optical isomers. The asymmetric conversion method, using (2 R,3R)-tartaric acid as the splitting agent and in the presence of butyraldehyde, allowed the simultaneous reaction of the racemization of L-proline and the salt crystallization of D-proline with (2 R,3R)-tartaric acid. The total yield was 82 %. |
D-Proline Preparation Products And Raw materials
| Raw materials | L-Proline |
| Preparation Products | (1R,2R)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID-->N-Boc-D-proline-->Fmoc-Pro-OH-->(S)-3-Amino-1-N-Boc-piperidine-->2-Pyrrolidinecarbonitrile,(2R)--->(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine-->Pamiparib-->BOC-D-PRO-OSU-->D-1-N-BOC-PROLINAMIDE-->METHYL-R-N-(METHOXY CARBONYL)-PROLINE ESTER-->1-(CHLOROACETYL)-D-PROLINE ETHYL ESTER-->(R)-1-Methacryloylpyrrolidine-2-carboxylic acid |
