75266-39-6

Upstream product

• 10332-17-9 Met-OMe 
• 501-53-1 benzyl chloroformate 
• 1152-62-1 Cbz-Met-OH 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 63-68-3 L-methionine 

Downstream Products

• 60027-55-6 (Z)-2-Benzyloxycarbonylamino-but-2-enoic acid methyl ester 
• 75266-40-9 N-benzyloxycarbonyl-L-α-vinylglycine methyl ester 
• 852693-74-4 methyl (S)-2-(tert-bytoxycarbonylamino)but-3-enoate 
• 72015-57-7 (Z)-2-(benzyloxycarbonylamino)but-2-enoic acid 
• 2483-62-7 (S)-2-aminobutyric acid methyl ester 
• 70363-18-7 N-<1-(Methoxycarbonyl)propyl>-α-methoxy-α-<(trifluoromethyl)phenyl>acetamide 
• 60027-61-4 methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate 
• 91109-12-5 (S)-((S)-3-Benzenesulfonyl-4,5-dihydro-isoxazol-5-yl)-benzyloxycarbonylamino-acetic acid methyl ester 
• 91109-13-6 (S)-((R)-3-Benzenesulfonyl-4,5-dihydro-isoxazol-5-yl)-benzyloxycarbonylamino-acetic acid methyl ester 
• 91028-68-1 [(S)-1-((S)-3-Benzenesulfonyl-4,5-dihydro-isoxazol-5-yl)-2-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester 
• 91028-69-2 [(S)-1-((R)-3-Benzenesulfonyl-4,5-dihydro-isoxazol-5-yl)-2-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester 
• 91028-77-2 [(S)-2-Hydroxy-2-methyl-1-((S)-3-methyl-4,5-dihydro-isoxazol-5-yl)-propyl]-carbamic acid benzyl ester 
• 91028-77-2 [(S)-2-Hydroxy-2-methyl-1-((R)-3-methyl-4,5-dihydro-isoxazol-5-yl)-propyl]-carbamic acid benzyl ester 
• 91028-48-7 (S)-3-<(benzyloxy)carbonyl>amino-2-methyl-4-penten-2-ol 

Relevant academic research and scientific papers

A convergent synthesis of carbocyclic sinefungin and its C-5 epimer

A convergent synthesis of carbocyclic sinefungin (2), its C-5 epimer 3a, and adenine-modified derivative 3b is described. The key features of our approach include the use of commercially available L-methionine and readily available (1R,4S)-4-hydroxy-2-cyclopentenyl acetate as starting materials, a cross-metathesis reaction, an enzymatic kinetic resolution, and a Staudinger reduction. The current synthesis is flexible and, therefore, provides convenient access to the synthesis of various carbocyclic sinefungin analogues for biological evaluation. A convergent synthesis of carbocyclic sinefungin (2), its C-5 epimer 3a, and adenine-modified derivative 3b is described. The key features of this approach include the use of commercially available L-methionine and readily available (1R,4S)-4-hydroxy-2-cyclopentenyl acetate, a cross-metathesis reaction, an enzymatic kinetic resolution, and a Staudinger reduction.

Enantioselective Synthesis of Non-Natural Aromatic α-Amino Acids

We present two complementary methods for the stereoselective synthesis of non-natural α-amino acids with aromatic or heteroaromatic side chains. One approach is based on the chemical transformation of methionine, whereas the other applies the stereoselective Myers alkylation of glycine. The resulting product types differ in the linker length between glycine and the aromatic substituent. Since methionine and pseudoephedrine are available in both absolute configurations, R- or S-configured enantiopure amino acids with either C2 or C3 linkers can be obtained on gram scales. In each case the key step of the synthesis is hydroboration of the unsaturated building blocks 9 and 17, followed by palladium-catalyzed Suzuki cross-coupling with aryl halides. Attention must in certain cases be paid to the stereochemical integrity when basic Suzuki conditions are applied. Our initial difficulties are reported as well as the final "racemization-proof" procedures. The protecting groups chosen for the α-amino acids should be compatible with solid-phase peptide synthesis. This was confirmed by the successful synthesis of a series of tripeptides.

Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers

The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system.

Structure and Stereochemistry of Three Phytotoxins, Syringomycin, Syringotoxin and Syringostatin, Produced by Pseudomonas syringae pv. syringae

The structures of two phytotoxins, syringomycin and syringotoxin, produced by Pseudomonas syringae pv. syringae, were determined.Several amino acid residues of syringomycin were different from those in the syringostatins.Syringotoxin B proved to be syringostatin A.The three kinds of phytotoxins showed close structural similarity, and the stereochemistry of their components was deduced and compared.

N-(BENZYLOXYCARBONYL)-L-VINYLGLYCINE METHYL ESTER FROM L-METHIONINE METHYL ESTER HYDROCHLORIDE

A reproducible, large scale and practical synthesis of N-(benzyloxycarbonyl)-L-vinylglycine methyl ester starting from L-methionine methyl ester hydrochloride is described.

L-Vinylglycine

Optically pure L-vinylglycine (1) has been synthesized from L-methionine in 54percent overall yield.The process consists in first preparing N-methionine methyl ester (9) which is then oxidized to methyl 2-amino>-