19728-63-3

Basic information

• Product Name: N-Cbz-L-Threonine
• Synonyms: N-ALPHA-BENZYLOXYCARBONYL-L-THREONINE;Z-L-THREONINE;Z-L-THR-OH;Z-THREONINE;Z-THR-OH;N-CARBOBENZYLOXY-L-THREONINE 98%;CARBOBENZYLOXY-L-THREONINE;Z-L-THREONINE extrapure
• CAS NO: 19728-63-3
• Molecular Formula: C₁₂H₁₅NO₅
• Molecular Weight: 253.25
• EINECS: 243-258-1
• Product Categories: Protected Amino Acids;PROTECTED AMINO ACID & PEPTIDES;Threonine [Thr, T];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Chiral Compounds;Cbz-Amino acid series
• Mol File: 19728-63-3.mol
• Article Data: 40

Chemical Properties

• Melting Point: 101-103 °C(lit.)
• Boiling Point: 396.45°C (rough estimate)
• Flash Point: 246.3 °C
• Appearance: white to light yellow crystal powder powder
• Density: 1.2499 (rough estimate)
• Vapor Pressure: 3.7E-11mmHg at 25°C
• Refractive Index: -4.9 ° (C=2, AcOH)
• Storage Temp.: −20°C
• Solubility: almost transparency in Methanol
• PKA: 3.58±0.10(Predicted)
• BRN: 2335409
• CAS DataBase Reference: N-Cbz-L-Threonine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-L-Threonine(19728-63-3)
• EPA Substance Registry System: N-Cbz-L-Threonine(19728-63-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 19728-63-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

N-Cbz-L-threonine is an N-Cbz-protected form of L-Threonine (T405500). L-Threonine is an essential amino acid that is commonly used as a feed and food additive. L-Threonine is produced in mass quantities by mutant Escherichia coli strains for research and food nutrition purposes. L-Threonine can be naturally found in fish and poultry, and is incorporated in some important proteins in the human body (such as hemoglobin and insulin).

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

Upstream product

• 72-19-5 D-threonine 
• 501-53-1 benzyl chloroformate 
• 72-19-5 L-threonine 
• 31139-36-3 dibenzyl dicarbonate 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 91285-94-8 O-benzyl S-(pyridin-2-yl)carbonothioate 
• 16966-09-9 N-benzyloxycarbonyl-O-t-butyl-L-threonine 
• 96452-48-1 benzyl pyridin-2-yl carbonate 
• 57710-80-2 1-benzyloxycarbonyl-1Hbenzo[d][1.2.3]triazole 
• 419533-86-1 benzyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 61668-49-3 sodium benzylcarbonate 
• 5241-58-7 L-Phenylalanine amide 
• 72-19-5 L-threonine 
• 112-60-7 Tetraethylene glycol 

Downstream Products

• 75624-32-7 N-benzyloxycarbonyl-DL-threonine benzyloxyamide 
• 75624-32-7 O-benzyl-α-N-CBZ-D,L-allo-threonine hydroxamate 
• 101937-71-7 N-benzyloxycarbonyl-O-chloroacetyl-threonine 
• 1195-19-3 DL-trans-5-Methyl-2-oxo-oxazolidin-4-carbonsaeure 
• 16597-50-5 N-benzyloxycarbonyl-DL-threonine benzyl ester 
• 85995-51-3 benzyl N-(benzyloxycarbonyl)-D,L-allothreoninate 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 34660-99-6 O-Trimethylsilyl-N-benzyloxycarbonyl-DL-threonin-trimethylsilylester 
• 18917-56-1 N-benzyloxycarbonyl-L-threonine pentachlorophenyl ester 
• 2483-53-6 Z-Thr-Ala-OMe 
• 2488-24-6 N-Benzyloxycarbonyl-L-threonyl-L-serin-methylester 
• 60644-11-3 C₁₄H₁₇N₃O₇ 
• 16305-79-6 N¹-<(benzyloxy)carbonyl>threonylglycine benzyl ester 
• 19649-01-5 Z-Thr-Phe-OMe 

Relevant articles and documents

Incorporation of chlorinated analogues of aliphatic amino acids during cell-free protein synthesis

3-Chloro-Abu and 4-chloro-Nva are biosynthetically incorporated into E. coli peptidyl-Pro cis-trans isomerase B, as substitutes for Val and Leu, respectively. The extent of incorporation is up to ～90%, and substituted protein is catalytically active. By contrast, 4-chloro-Val is not an effective replacement for Ile.

Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate

We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule, there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure?activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.

PROCESS AND INTERMEDIATES FOR SYNTHESIS OF PEPTIDE COMPOUNDS

Disclosed is a new process and intermediates for preparing dipyrrolidine peptide compounds such as, for example, rapastinel. Advantageously, the process may be industrially scalable and cost-effective and use less toxic reagents and/or solvents. Further, the process may be used to prepare peptide compounds having improved purity.