Benzyloxycarbonyl-L-proline
Z-PRO-OH · CBZ-PRO-OH · Z-Pro · CBZ-L-PROLINE · N-CBZ-L-PROLINE · CBZ-L-Pro · Z-L-PRO-OH · Z-PROLINE
Identifiers & Physical Properties
| CAS No. | 1148-11-4 |
|---|---|
| Molecular formula | C13H15NO4 |
| Average molar mass | 249.26 g/mol |
| Monoisotopic mass | 249.10010796 g/mol |
| SMILES | O=C(O)[C@@H]1CCCN1C(=O)OCc1ccccc1 |
| InChIKey | JXGVXCZADZNAMJ-NSHDSACASA-N |
| PubChem CID | 101987 |
| ChEMBL | CHEMBL3276375 |
| EC No. | 214-557-4 |
| DTXSID | DTXSID40150856 |
Chemical & Physical Properties
| XLogP | 1.7 |
|---|---|
| Topological polar surface area | 66.8 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 4 |
| Heavy atoms | 18 |
| Formal charge | 0 |
| Complexity | 312 |
| Melting point | 75-77 °C |
| alpha | -60 º (c=2,AcOH) |
| Boiling point | 392.36°C (rough estimate) |
| Density | 1.1952 (rough estimate) |
| Refractive index | -40 ° (C=2, EtOH) |
| Storage conditions | Sealed in dry,Room Temperature |
| Solubility | Solubility in methanol, almost transparency. |
| Physical state | Crystalline Powder or Crystals |
| pKa (acidity coefficient) | 3.99±0.20(Predicted) |
| Color | White to off-white |
| optical activity | [α]20/D 42°, c = 2 in ethanol |
| BRN | 88579 |
| Major applications | peptide synthesis |
| InChI | InChI=1S/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m0/s1 |
| InChIKey | JXGVXCZADZNAMJ-NSHDSACASA-N |
| SMILES | N1(C(OCC2=CC=CC=C2)=O)CCC[C@H]1C(O)=O |
| CAS DataBase Reference | 1148-11-4(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | H2BS8M5FPP |
| UNSPSC Code | 12352209 |
| NACRES | NA.22 |
| GHS pictogram | GHS05 |
| Signal word | Danger |
| GHS hazard statements | H318 |
| GHS precautionary statements | P271-P261-P280 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xn |
| Risk statements (R) | 62-36/37/38-20/21/22 |
| Safety statements (S) | 22-24/25-36-26 |
| Water hazard class (WGK) | 3 |
| RTECS number | UY0745000 |
| Hazard class | IRRITANT |
| Customs code | 29339900 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 37.5% (3 of 8) of reports.DangerH315 (37.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 8 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (37.5%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| RTECS number | UY0745000 |
| Customs code | 29339900 |
| Risk statements (R) | 62-36/37/38-20/21/22 |
| Signal word | Danger |
| GHS pictogram | GHS05 |
| Hazard symbols | Xn |
| Safety statements (S) | 22-24/25-36-26 |
| Hazard class | IRRITANT |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H318 |
| GHS precautionary statements | P271-P261-P280 |
Applications & Uses
Uses
N-(Benzyloxycarbonyl)-L-proline is a potent in vitro and in vivo inhibitor of prolidase; a specific peptidase that cleaves dipeptides with a C-terminal prolyl and hydroxylprolyl residue. It is also used in the synthesis of N-(L-Prolyl)-β-alanine which is a derivative of the naturally occurring beta amino acid β-Alanine.
Preparation & Synthesis
Preparation
Caution! All procedures must be carried out in an efficient fume cupboard, wearing latex gloves and chemical-proof safety goggles. ι-Proline (10.0 g, 8.7 mmol) was dissolved in 2 m sodium hydroxide solution (40 mL), and the solution was cooled to ice-water temperature. Z-Cl (20.5 g, 12 mmol) was added portionwise, with vigorous stirring or occasional shaking, over a period of 30 min at 0–5 °C to the solution of l-proline. The ice bath was then removed and stirring or occasional shaking was continued for 30 min while the reaction mixture warmed to room temperature. The mixture was then acidified to Congo red by the gradual addition of concentrated hydrochloric acid, and the oil was extracted into ethyl acetate. The extract was dried over magnesium sulfate, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was extracted/triturated with warm tetrachloromethane. The washings were decanted and the residue was further purified by recrystallization from ethyl acetate/petroleum ether.