7451-74-3

Usage

InChI:InChI=1/C8H15NO3S/c1-6(10)9-7(4-5-13-3)8(11)12-2/h7H,4-5H2,1-3H3,(H,9,10)

Upstream product

• 10332-17-9 DL-methionine methyl ester 
• 1115-47-5 N-acetyl-DL-methionine 
• 77-76-9 2,2-dimethoxy-propane 
• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 59-51-8 DL-methionine 
• 126027-78-9 N-Acetyl-L-methionine sulfoxide methyl ester 

Downstream Products

• 63-68-3 L-methionine 
• 35671-83-1 methyl N-acetylmethionine 
• 65-82-7 N-acetyl-l-methionine 
• 1115-47-5 N-acetyl-DL-methionine 

Relevant academic research and scientific papers

Comparison of liquid chromatography-isotope ratio mass spectrometry (LC/IRMS) and gas chromatography-combustion-isotope ratio mass spectrometry (GC/C/IRMS) for the determination of collagen amino acid δ13C values for palaeodietary and palaeoecological reconstruction

Results are presented of a comparison of the amino acid (AA) δ13C values obtained by gas chromatography-combustion-isotope ratio mass spectrometry (GC/C/IRMS) and liquid chromatography-isotope ratio mass spectrometry (LC/IRMS). Although the primary focus was the compound-specific stable carbon isotope analysis of bone collagen AAs, because of its growing application for palaeodietary and palaeoecological reconstruction, the results are relevant to any field where AA δ13C values are required. We compare LC/IRMS with the most up-to-date GC/C/IRMS method using N-acetyl methyl ester (NACME) AA derivatives. This comparison involves the analysis of standard AAs and hydrolysates of archaeological human bone collagen, which have been previously investigated as N-trifluoroacetyl isopropyl esters (TFA/IP). It was observed that, although GC/C/IRMS analyses required less sample, LC/IRMS permitted the analysis of a wider range of AAs, particularly those not amenable to GC analysis (e.g. arginine). Accordingly, reconstructed bulk δ13C values based on LC/IRMS-derived δ13C values were closer to the EA/IRMS-derived δ13C values than those based on GC/C/IRMS values. The analytical errors for LC/IRMS AA δ13C values were lower than GC/C/IRMS determinations. Inconsistencies in the δ13C values of the TFA/IP derivatives compared with the NACME- and LC/IRMS-derived δ13C values suggest inherent problems with the use of TFA/IP derivatives, resulting from: (i) inefficient sample combustion, and/or (ii) differences in the intra-molecular distribution of δ13C values between AAs, which are manifested by incomplete combustion. Close similarities between the NACME AA δ13C values and the LC/IRMS-derived δ13C values suggest that the TFA/IP derivatives should be abandoned for the natural abundance determinations of AA δ13C values.

Use of enantio-, chemo- and regioselectivity of acylase I. Resolution of polycarboxylic acid esters

Acylase I was used to catalyze the enantioselective butanolysis of trimethyl 2-[(carboxymethyl)oxy]succinate (E=30) and N-carboxymethylaspartate (E=9) exclusively at the most sterically hindered of the three ester groups (the position α to the asymmetric centre). Gram-scale resolution allowed the preparation of the less reactive trimethyl (S)-2-[(carboxymethyl)oxy]succinate (96% e.e.), that of the (R)-butyldimethyl regioisomer (78% e.e.) at 55% conversion and finally the preparation of the corresponding trisodium carboxylate by saponification. Acylase I was shown to transform (±)-methyl N-acetylmethionine and (±)-valine to the corresponding (S)-amino acids through ester hydrolysis-N-acetyl transfer sequence with absolute chemo- and enantioselectivity. Butanolysis of methyl N-acetylmethionine stopped in the formation of the butyl ester (E=12), the valine derivative being totally unreactive.

SYNTHESIS OF FLUORINATED DERIVATIVES OF METHIONINE AND 5'-DEOXY-5'-(METHYLTHIO)-ADENOSINE USING THE McCARTHY TRANSFORMATION OF SULFOXIDES TO α-FLUORO THIOETHERS

Treatment of N-acetylmethionine sulfoxide methyl ester with diethylaminosulfur trifluoride (DAST) or dimethylaminosulfur trifluoride (meDAST) yielded N-acetyl-S-(monofluoromethyl)homocysteine methyl ester as the sole fluorinated product.In contrast, treatment of 2',3'-di-O-acetyl-5'-(methylthio)adenosine sulfoxide with DAST or meDAST unexpectedly produced three novel fluorinated products.

Decarboxylation of 1-Aminocyclopropanecarboxylic Acid and Its Derivatives

The question of whether the title compounds could be decarboxylated to cyclopropanone derivatives was answered in the affirmative by the following observations. (1) Compound 11a was decarboxylated by 1,2,3-indantrione in acetonitrile, benzene, or methanol.The initially formed intermediate could be trapped by N-phenylmaleimide (to form 3), by diethyl azodicarboxylate (to form an unstable adduct), by ninhydrin itself (to form 5) or by a proton (in methanol, to form 8). (2) Compound 11d was decarboxylated by phenylbis(trifluoroacetato-O)iodine to yield carbinolamine 12d.cis-2,3-Dideuterio-11d yielded cis-2,3-dideuterio-12d under the same conditions. (3) ACC was decarboxylated by phenanthroquinone to yield oxazole 9, probably by way of oxazoline 10.

RHODIUM CATALYZED REDUCTIVE ESTERIFICATION REACTIONS

Reductive esterification occurs when unsaturated acids are treated with hydrogen in alcohol using either rhodium trichloride or the dimer of chloro(1,5-hexadiene)rhodium(I) as the catalyst.Saturated acids containing appropriate functional groups are also esterified under the same conditions.