1195-20-6

Upstream product

• 80-68-2 DL-threonine 
• 501-53-1 benzyl chloroformate 
• 16874-73-0 (RS)-4-((SR)-1-hydroxy-ethyl)-oxazolidine-2,5-dione 
• 72-19-5 L-threonine 
• 127870-55-7 Benzoic acid (4R,5R)-5-methyl-2-oxo-oxazolidin-4-ylmethyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 4378-13-6 (O-tert-butyl)-L-threonine 
• 42583-85-7 N₆-(L-threonylcarbamoyl)adenosine-5'-monophosphate 
• 119221-16-8 (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid 
• 37791-35-8 3-benzoyl-5t-methyl-2-oxo-oxazolidine-4r-carboxylic acid benzyl ester 
• 37791-40-5 N-benzoyl-O-chlorocarbonyl-DL-threonine benzyl ester 
• 37791-39-2 N-benzoyl-O-chlorocarbonyl-DL-threonine methyl ester 
• 37791-33-6 3-benzoyl-5t-methyl-2-oxo-oxazolidine-4r-carboxylic acid 
• 37791-37-0 3-benzoyl-5t-methyl-2-oxo-oxazolidine-4r-carbonyl chloride 

Downstream Products

• 83791-43-9 methyl (4S,5R)-5-methyl-2-carbonyloxazolidine-4-carboxylate 
• 72-19-5 L-threonine 
• 171563-10-3 benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate 
• 1310374-65-2 (4R,5R)-5-methyl-4-(2-oxo-2-phenylethyl)oxazolidin-2-one 

Relevant academic research and scientific papers

Mechanism of N6-threonylcarbamoyladenonsine (t6A) biosynthesis: Isolation and characterization of the intermediate threonylcarbamoyl-AMP

Genetic and biochemical studies have recently implicated four proteins required in bacteria for the biosynthesis of the universal tRNA modified base N6-threonylcarbamoyl adenosine (t6A). In this work, t6A biosynthesis in Bacillus subtilis has been reconstituted in vitro and found to indeed require the four proteins YwlC (TsaC), YdiB (TsaE), YdiC (TsaB) and YdiE (TsaD). YwlC was found to catalyze the conversion of l-threonine, bicarbonate/CO2 and ATP to give the intermediate l-threonylcarbamoyl- AMP (TC-AMP) and pyrophosphate as products. TC-AMP was isolated by HPLC and characterized by mass spectrometry and 1H NMR. NMR analysis showed that TC-AMP decomposes to give AMP and a nearly equimolar mixture of l-threonine and 5-methyl-2-oxazolidinone-4-carboxylate as final products. Under physiological conditions (pH 7.5, 37 °C, 2 mM MgCl2), the half-life of TC-AMP was measured to be 3.5 min. Both YwlC (in the presence of pyrophosphatase) and its Escherichia coli homologue YrdC catalyze the formation of TC-AMP while producing only a small molar fraction of AMP. This suggests that CO2 and not an activated form of bicarbonate is the true substrate for these enzymes. In the presence of pyrophosphate, both enzymes catalyze clean conversion of TC-AMP back to ATP. Purified TC-AMP is efficiently processed to t6A by the YdiBCE proteins in the presence of tRNA substrates. This reaction is ATP independent in vitro, despite the known ATPase activity of YdiB. The estimated rate of conversion of TC-AMP by YdiBCE to t6A is somewhat lower than the initial rate from l-threonine, bicarbonate and ATP, which together with the stability data, is consistent with previous studies that suggest channeling of this intermediate.

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.

HEPATITIS C VIRUS INHIBITORS

The present disclosure relates to compounds, compositions and methods for the treatment of Hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

RAPID SYNTHESIS OF β-HYDROXY-α-AMINO ACIDS, SUCH AS L-THREONINE, β-HYDROXYPHENYLALANINE, AND β-HYDROXYLEUCINE, VIA AN APPLICATION OF THE SHARPLESS ASYMMETRIC EPOXIDATION

The optically active epoxy alcohols 6abc, prepared by a Sharpless kinetic resolution-epoxidation process, were converted to the optically pure β-hydroxy-α-amino acids 1abc in four steps and high overall yield.