Name | N-Carbobenzyloxy-L-threonine |
Synonyms | Z-Thr Z-L-Thr Z-Thr-OH Z-THR-OH Z-L-THR-OH Z-THREONINE Z-L-THREONINE Cbz-L-threonine N-Cbz-L-Threonine N-Carbobenzyloxy-L-threonine N-benzyloxycarbonyl-l-threonine N-[(benzyloxy)carbonyl]threonine N-ALPHA-BENZYLOXYCARBONYL-L-THREONINE benzyl [(1S,2R)-1-carbamoyl-2-hydroxypropyl]carbamate (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoate |
CAS | 19728-63-3 |
EINECS | 243-258-1 |
InChI | InChI=1/C12H16N2O4/c1-8(15)10(11(13)16)14-12(17)18-7-9-5-3-2-4-6-9/h2-6,8,10,15H,7H2,1H3,(H2,13,16)(H,14,17)/t8-,10+/m1/s1 |
Molecular Formula | C12H15NO5 |
Molar Mass | 253.25 |
Density | 1.2499 (rough estimate) |
Melting Point | 101-103°C(lit.) |
Boling Point | 396.45°C (rough estimate) |
Specific Rotation(α) | -4.7 º (c=4, acetic acid) |
Flash Point | 261.3°C |
Solubility | almost transparency in Methanol |
Vapor Presure | 3.7E-11mmHg at 25°C |
Appearance | White to light yellow crystal powder |
Color | White to Almost white |
BRN | 2335409 |
pKa | 3.58±0.10(Predicted) |
Storage Condition | Sealed in dry,Store in freezer, under -20°C |
Refractive Index | -4.9 ° (C=2, AcOH) |
MDL | MFCD00065948 |
Use | Used for biochemical reagents, peptide synthesis. |
Hazard Symbols | Xn - Harmful |
Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
HS Code | 29242990 |
preparation | add 50mL of L-Thr(30mmol) and cooled saturated Na2CO3 solution into a 250mL reaction bottle, and stir and dissolve in an ice bath. Drop 20mL of Z-OSu(39.4mmol) acetone solution into the reaction bottle; Stir the reaction at 25 ℃, TLC-UV fluorescence and ninhydrin color method monitor the reaction process. After the reaction, add H2O 20mL, extract with Et2O(30mL × 2) at pH>9, collect the aqueous phase, adjust the pH to 3~4 with 1.5NHCl, extract with EtOAc(30mL × 3), combine the organic phase, wash with saturated NaCl solution (25mL × 2), dry with anhydrous Na2SO4, check the purity by TLC-ultraviolet fluorescence and ninhydrin color development method, and evaporate under reduced pressure, vacuum drying to obtain a yellowish oily liquid N-benzyloxycarbonyl-L-threonine, which is stored at low temperature. |
Use | CBZ-L-threonine is the N-Cbz protected form of L-threonine (T405500). L-threonine is an essential amino acid and is commonly used as a feed and food additive. The mutant strain of Escherichia coli produced large quantities of L-threonine for research and food nutrition purposes. L-threonine is naturally found in fish and poultry and is incorporated into some of the body's important proteins, such as hemoglobin and insulin. Used for biochemical reagents and peptide synthesis. |