40216-74-8

Upstream product

• 100-52-7 benzaldehyde 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 69630-60-0 methyl D-methioninate hydrochloride 
• 63-68-3 L-methionine 

Downstream Products

• 1384559-59-4 methyl (2S)-2-{[phenyl-(S)-(dimethoxyphosphoryl)methyl]amino}-4-methylsulfanylbutyrate 
• 1384559-73-2 methyl (2S)-2-{[phenyl-(R)-(dimethoxyphosphoryl)methyl]amino}-4-methylsulfanylbutyrate 
• 112674-82-5 (S)-2-((R)-2-Amino-3-phenyl-propionylamino)-4-methylsulfanyl-butyric acid 
• 112674-80-3 (S)-4-Methylsulfanyl-2-[(R)-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-3-phenyl-propionylamino]-butyric acid 
• 452282-35-8 C₁₃H₁₈N₂O₃S 
• 452282-27-8 N-benzyl-L-methionine methyl ester 
• 112674-76-7 (S)-4-Methylsulfanyl-2-[(3R,4S)-2-oxo-3-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-4-phenyl-azetidin-1-yl]-butyric acid methyl ester 

Relevant academic research and scientific papers

Synthesis and Penicillin-binding Protein Inhibitory Assessment of Dipeptidic 4-Phenyl-β-lactams from α-Amino Acid-derived Imines

Monocyclic β-lactams revive the research field on antibiotics, which are threatened by the emergence of resistant bacteria. A six-step synthetic route was developed, providing easy access to new 3-amino-1-carboxymethyl-4-phenyl-β-lactams, of which the penicillin-binding protein (PBP) inhibitory potency was demonstrated biochemically.

Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1′-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators

Developing specific chemical functionalities to deploy in biological environments for targeted enzyme inactivation lies at the heart of mechanism-based inhibitor development but also is central to other protein-tagging methods in modern chemical biology including activity-based protein profiling and proteolysis-targeting chimeras. We describe here a previously unknown class of potential PLP enzyme inactivators; namely, a family of quaternary, α-(1′-fluoro)vinyl amino acids, bearing the side chains of the cognate amino acids. These are obtained by the capture of suitably protected amino acid enolates with β,β-difluorovinyl phenyl sulfone, a new (1′-fluoro)vinyl cation equivalent, and an electrophile that previously eluded synthesis, capture and characterization. A significant variety of biologically relevant AA side chains are tolerated including those for alanine, valine, leucine, methionine, lysine, phenylalanine, tyrosine, and tryptophan. Following addition/elimination, the resulting transoid α-(1′-fluoro)-β-(phenylsulfonyl)vinyl AA-esters undergo smooth sulfone-stannane interchange to stereoselectively give the corresponding transoid α-(1′-fluoro)-β-(tributylstannyl)vinyl AA-esters. Protodestannylation and global deprotection then yield these sterically encumbered and densely functionalized quaternary amino acids. The α-(1′-fluoro)vinyl trigger, a potential allene-generating functionality originally proposed by Abeles, is now available in a quaternary AA context for the first time. In an initial test of this new inhibitor class, α-(1′-fluoro)vinyllysine is seen to act as a time-dependent, irreversible inactivator of lysine decarboxylase from Hafnia alvei. The enantiomers of the inhibitor could be resolved, and each is seen to give time-dependent inactivation with this enzyme. Kitz-Wilson analysis reveals similar inactivation parameters for the two antipodes, L-α-(1′-fluoro)vinyllysine (Ki = 630 ± 20 μM; t1/2 = 2.8 min) and D-α-(1′-fluoro)vinyllysine (Ki = 470 ± 30 μM; t1/2 = 3.6 min). The stage is now set for exploration of the efficacy of this trigger in other PLP-enzyme active sites.

Addition of dimethyl phosphite to imines bearing the L -methionine moiety and its surprisingly poor chiral assistance

The preparation of methyl 2-{[(dimethoxyphosphoryl)-methyl]-amino}-4- methyl- sulfanylbutyrates (3a-e) by the addition of dimethyl phosphite to 2-(methylidenamino)-4-methylsulfanylbutyric acid methyl esters (2a-e) is described. The nearly nonexisting dias

A facile stereospecific synthesis of α-hydrazino esters

A convenient route to make α-hydrazino esters from their corresponding α-amino esters is reported. A key step is selective nitrosamine reduction using activated Zn, conc. HCl, and methanol at low temperatures giving nearly quantitative yields of the pure α-hydrazino esters.

Method for preparation of sphingoid bases

The present invention provides a series of non-toxic compounds which function to inhibit the activity of S-1-P aldolase in respect to its cleavage of S-1-P. These inhibitors are described by the compounds of formula I STR1 wherein R is a radical containing 1 to 15 carbon atoms, a halogen, or hydrocarbon, R' is an organic radical or hydrogen, and R" is --NH3+ or --NH--NH +, with the proviso that, when R is CH3 (CH)12 (CH=CH) and R' is hydrogen, R" is --NH--NH3+. A method for preparing such compounds, which may generally be described as 1-phosphate derivatives of compounds which include a 2-amino-1,3-alcohol radical is also disclosed.