119221-16-8

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid is used as a building block in the synthesis of peptides and proteins for various pharmaceutical applications. Its role as a protecting group for the carboxyl group of glutamic acid allows for the controlled formation of peptide bonds, which is crucial in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid is used as a protecting group for the carboxyl group of glutamic acid. This enables chemists to carry out selective reactions and synthesize complex peptide structures with greater precision and control.
Used in Research and Development:
(2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid is employed in research and development for the study of peptide synthesis, protein structure, and function. Its use as a protecting group allows researchers to investigate the properties and interactions of peptides and proteins in a controlled manner, contributing to the advancement of scientific knowledge in these areas.

Upstream product

• 72-19-5 D-threonine 
• 501-53-1 benzyl chloroformate 
• 80-68-2 DL-threonine 
• 72-19-5 rac-allo-threonine 
• 632-20-2 D-Threonine 
• 24830-94-2 D-allo-threonine 
• 100157-61-7 (D)-allo-threonine hydrochloride 
• 100157-53-7 N-carbobenzyloxy-D-allo-threonine methyl ester 

Downstream Products

• 34660-99-6 O-Trimethylsilyl-N-benzyloxycarbonyl-DL-threonin-trimethylsilylester 
• 67646-42-8 4-Benzyloxycarbonylamino-2-cyano-5-hydroxy-3-oxo-hexanoic acid ethyl ester 
• 78464-34-3 2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-but-2-enoic acid ethyl ester 
• 78464-32-1 (E)-2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-but-2-enoic acid ethyl ester 
• 78464-33-2 (E)-2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-pent-2-enoic acid ethyl ester 
• 78464-36-5 (E)-2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-4-methyl-pent-2-enoic acid ethyl ester 
• 78464-35-4 (E)-2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-hex-2-enoic acid ethyl ester 
• 98132-34-4 Z-DL-Thr-DMPir 
• 23161-28-6 N-Carbobenzoxy-DL-threoninaethylester 
• 112026-37-6 ethyl 2-(benzyloxycarbonylamino)acetoacetate 
• 78464-56-9 2-((E)-2-Benzyloxycarbonylamino-but-2-enoylamino)-3-methyl-but-2-enoic acid ethyl ester 
• 78464-38-7 (E)-2-(2-Benzyloxycarbonylamino-3-methanesulfonyloxy-butyrylamino)-but-2-enoic acid ethyl ester 
• 78464-40-1 2-(2-Benzyloxycarbonylamino-3-methanesulfonyloxy-butyrylamino)-3-methyl-but-2-enoic acid ethyl ester 
• 78464-39-8 (E)-2-(2-Benzyloxycarbonylamino-3-methanesulfonyloxy-butyrylamino)-pent-2-enoic acid ethyl ester 

Relevant academic research and scientific papers

One enantiomeric fluorescent sensor pair to discriminate four stereoisomers of threonines

The BINOL-amino alcohol enantiomeric pair (S)-1 and (R)-1 are discovered to conduct both enantioselective and diastereoselective fluorescent discrimination of the four stereoisomers of threonine derivatives. This study utilizes different fluorescence resp

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.

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.

Potent α-amino-β-lactam carbamic acid ester as NAAA inhibitors. Synthesis and structure-activity relationship (SAR) studies

4-Cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate (3b) is a potent, selective and systemically active inhibitor of intracellular NAAA activity, which produces profound anti-inflammatory effects in animal models. In the present work, we describe structure-activity relationship (SAR) studies on 3-aminoazetidin-2-one derivatives, which have led to the identification of 3b, and expand these studies to elucidate the principal structural and stereochemical features needed to achieve effective NAAA inhibition. Investigations on the influence of the substitution at the β-position of the 2-oxo-3-azetidinyl ring as well as on the effect of size and shape of the carbamic acid ester side chain led to the discovery of 3ak, a novel inhibitor of human NAAA that shows an improved physicochemical and drug-like profile relative to 3b. This favourable profile, along with the structural diversity of the carbamic acid chain of 3b, identify this compound as a promising new tool to investigate the potential of NAAA inhibitors as therapeutic agents for the treatment of pain and inflammation.

CARBAMATE DERIVATIVES OF LACTAM BASED N-ACYLETHANOLAMINE ACID AMIDASE (NAAA) INHIBITORS

Described herein are compounds and pharmaceutical compositions which inhibit N-acylethanolamine acid amidase (NAAA). Described herein are methods for synthesizing the compounds set forth herein and methods for formulating these compounds as pharmaceutical compositions which include these compounds. Also described herein are methods of inhibiting NAAA in order to sustain the levels of palmitoylethanolamide (PEA) and other N-acylethanolamines (NAE) that are substrates for NAAA, in conditions characterized by reduced concentrations of NAE. Also, described here are methods of treating and ameliorating pain, inflammation, inflammatory diseases, and other disorders in which modulation of fatty acid ethanolamides is clinically or therapeutically relevant or in which decreased levels of NAE are associated with the disorder.

N -(2-Oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors: Synthesis and structure-activity and structure-property relationships

The β-lactone ring of N-(2-oxo-3-oxetanyl)amides, a class of N-acylethanolamine acid amidase (NAAA) inhibitors endowed with anti-inflammatory properties, is responsible for both NAAA inhibition and low compound stability. Here, we investigate the structure-activity and structure-property relationships for a set of known and new β-lactone derivatives, focusing on the new class of N-(2-oxo-3-oxetanyl)carbamates. Replacement of the amide group with a carbamate one led to different stereoselectivity for NAAA inhibition and higher intrinsic stability, because of the reduced level of intramolecular attack at the lactone ring. The introduction of a syn methyl at the β-position of the lactone further improved chemical stability. A tert-butyl substituent in the side chain reduced the reactivity with bovine serum albumin. (2S,3R)-2-Methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester (27, URB913/ARN077) inhibited NAAA with good in vitro potency (IC50 = 127 nM) and showed improved stability. It is rapidly cleaved in plasma, which supports its use for topical applications.

Total synthesis of (-)-lemonomycin

When life gives you lemons: An efficient and convergent enantioselective total synthesis of (-)-lemonomycin, which shows potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF), is presented. The key reaction steps are a Hosomi-Sakurai-type cyclization, a thermodynamically controlled Pictet-Spengler reaction, and a glycosidation reaction with lemonose (see scheme). Copyright

Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative

In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs. 2009 American Chemical Society.

Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment

The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland-Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments are also disclosed. The relative and absolute stereochemistry of this natural product was determined by fragment coupling with the two enantiomers of the side chain fragment.

Synthesis and biological activity of piperazine-Based dual MMP-13 and TNF-α converting enzyme inhibitors

A series of novel MMP-13 and TNF-α converting enzyme inhibitors based on piperazine 2-hydroxamic acid scaffolds are described. The TACE, MMP-1 and MMP-13 activity of these inhibitors as well as the effect of substitution of the piperazine nitrogen and the P-1′ benzyloxy tailpiece is discussed. Moderate in vivo activity is observed with several members of this group.