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

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

Uses

Used in Pharmaceutical Industry:
N-Cbz-L-Threonine is used as a building block in the synthesis of various pharmaceutical compounds. Its N-Cbz protection allows for selective reactions and prevents unwanted side reactions, making it a valuable intermediate in the development of new drugs.
Used in Food and Nutrition Industry:
N-Cbz-L-Threonine is used as a feed and food additive to enhance the nutritional value of products. As an essential amino acid, it contributes to the overall protein content and supports the growth and maintenance of various tissues in the body.
Used in Research and Development:
N-Cbz-L-Threonine is used as a research compound to study the properties and functions of L-Threonine in biological systems. Its N-Cbz protection allows for the investigation of its role in protein synthesis and other metabolic pathways, as well as its potential therapeutic applications.

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 
• 72-19-5 L-threonine 
• 112-60-7 Tetraethylene glycol 
• 1885-14-9 phenyl chloroformate 
• 80-68-2 DL-threonine 

Downstream Products

• 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 
• 19649-01-5 Z-Thr-Phe-OMe 
• 19649-01-5 N-Benzyloxycarbonyl-L-threonyl-L-phenylalanin-methylester 
• 84500-41-4 N-benzyloxycarbonyl-L-threonine benzyl ester 
• 67646-42-8 4-Benzyloxycarbonylamino-2-cyano-5-hydroxy-3-oxo-hexanoic acid ethyl ester 
• 27482-74-2 N-Benzyloxycarbonyl-L-threonyl-glycin-ethylester 
• 16879-84-8 N-(benzyloxycarbonyl)-L-threonine p-nitrobenzyl ester 
• 5854-78-4 (2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate 

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.

EP300/CREBBP INHIBITOR

The present invention provides a compound having excellent histone acetyltransferase inhibitory activity against EP300 and/or CREBBP, or a pharmacologically acceptable salt thereof. The compound is represented by the following formula (1) or a pharmacologically acceptable salt thereof: wherein ring Q1, ring Q2, R1, R2, R3 and R4 respectively have the same meanings as defined in the specification.

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.

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.

L-threonine-linked dihydroartemisinin-fluoroquinolone conjugates, intermediates thereof, and preparation methods and uses of conjugates and intermediates

The invention discloses L-threonine-linked dihydroartemisinin-fluoroquinolone conjugates represented by formula I, intermediates represented by formula II, preparation methods of the compounds of formula I and formula II, and uses of the compounds of the formula I in the preparation of drugs for resisting mycobacterium tuberculosis or/and drugs for lowering blood lipids.

Strategy for O-alkylation of serine and threonine from serinyl and threoninyl acetic acids by photoinduced decarboxylative radical reactions: Connection between serine/threonine and carbohydrates/amino acids at the side chain

O-Alkylations of serine and threonine derivatives at the hydroxy group were achieved using photoinduced decarboxylative radical reactions of serinyl and threoninyl acetic acids with an organic photocatalyst without racemization under mild conditions. Photoinduced decarboxylative radical additions of serinyl and threoninyl acetic acids to electron-deficient alkenes provided linked serine and threonine with carbohydrates and amino acids at the side chain. In addition, O-methylations containing deuterium and O-benzylation of serine were performed under similar photochemical conditions.

SPIRO-LACTAM NMDA MODULATORS AND METHODS OF USING SAME

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

SPIRO-LACTAM AND BIS-SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

PROCESSES FOR SYNTHESIS OF DIPYRROLIDINE PEPTIDE COMPOUNDS

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Highly stable triple helix formation by homopyrimidine (l)-acyclic threoninol nucleic acids with single stranded DNA and RNA

Acyclic (l)-threoninol nucleic acid (aTNA) containing thymine, cytosine and adenine nucleobases were synthesized and shown to form surprisingly stable triplexes with complementary single stranded homopurine DNA or RNA targets. The triplex structures consist of two (l)-aTNA strands and one DNA or RNA, and these triplexes are significantly stronger than the corresponding DNA or RNA duplexes as shown in competition experiments. As a unique property the (l)-aTNAs exclusively form triplex structures with DNA and RNA and no duplex structures are observed by gel electrophoresis. The results were compared to the known enantiomer (d)-aTNA, which forms much weaker triplexes depending upon temperature and time. It was demonstrated that (l)-aTNA triplexes are able to stop primer extension on a DNA template, showing the potential of (l)-aTNA for antisense applications. This journal is