329912-92-7

Upstream product

• 2491-20-5 L-alanine methyl ester hydrochloride 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 10065-72-2 L-Alanine methyl ester 

Downstream Products

• 455333-80-9 (S)-methyl 2-(N-allyl-4-nitrophenylsulfonamido)propanoate 
• 486439-58-1 (2S)-methyl 2-(N-(but-3-en-1-yl)4-nitrobenzenesulfonamido)propanoate 
• 610800-48-1 (S)-methyl 2-(N-methyl-4-nitrobenzenesulfonamido)propanoate 
• 884494-17-1 (S)-2-[(4-Nitro-benzenesulfonyl)-pent-4-enyl-amino]-propionic acid methyl ester 
• 916049-32-6 2-[(4-nitrobenzenesulfonyl)trimethylsilanylmethylamino]propionic acid methyl ester 
• 10065-72-2 L-Alanine methyl ester 
• 1243654-80-9 N-ethyl-N-nosyl-L-alanine methyl ester 
• 1613295-37-6 (3aS,6S,6aS)-6-methyl-5-[(4-nitrophenyl)sulfonyl]-3,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole 
• 1613295-38-7 (3aS,6S,6aR)-6-methyl-5-[(4-nitrophenyl)sulfonyl]-3,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole 
• 1613295-39-8 C₁₂H₁₄N₂O₄S 
• 1613295-36-5 (S)-N-allyl-N-[1-(2-tosylhydrazono)propan-2-yl]-4-nitrobenzenesulfonamide 
• 1613295-35-4 (S)-N-allyl-N-(1-oxopropan-2-yl)-4-nitro-benzenesulfonamide 
• 1613295-40-1 (S)-N-allyl-N-(1-hydroxypropan-2-yl)-4-nitro-benzenesulfonamide 
• 59724-75-3 N-(p-nitrophenylsulfonyl)-(S)-alanine 

Relevant academic research and scientific papers

MACROCYCLIC COMPOUNDS FOR THE TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement factor D or a pharmaceutically acceptable salt or composition thereof are provided. The inhibitors described herein target factor D and inhibit or regulate the complement cascade. The inhibitors of factor D described herein reduce excessive activation of complement.

Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds

We herein report the palladium(II)-catalyzed bromination and iodination of a variety of α-hydrogen-containing carboxylic acid and amino acid-derived amides. These reactions are exclusively enabled by quinoline-type ligands. The halogenated products obtained in this reaction are highly versatile and rapidly undergo further diversification. Further, we report the first example of a free carboxylic acid-directed Pd(II)-catalyzed C(sp3)-H bromination, enabled by quinoline ligands.

Macrocyclic peptidomimetic inhibitors of β-secretase (BACE): First X-ray structure of a macrocyclic peptidomimetic-BACE complex

The synthesis of novel macrocyclic peptidomimetic inhibitors of the enzyme BACE1 is described. These macrocycles are derived from a hydroxyethylene core structure. Compound 7 was co-crystallized with BACE1 and the X-ray structure of the complex elucidated at 1.6 A resolution. This molecule inhibits the production of the Aβ peptide in HEK293 cells overexpressing APP751sw.

Building functionalized peptidomimetics: Use of electroauxiliaries for introducing N-acyliminium ions into peptides

A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

A general approach to dehydro-Freidinger lactams: Ex-chiral pool synthesis and spectroscopic evaluation as potential reverse turn inducers

Starting from natural α-amino acids, a practical synthesis of the dehydro-Freidinger lactams 9a-h based on the ring-closing olefin metathesis reaction was investigated. The presented examples comprise 6-, 7-, 8-, 9-, and 10-membered cyclic dipeptide mimics. Structural variations were demonstrated. We approached the metathesis precursors 8a-h employing an N-alkylation/peptide-coupling strategy. Subsequent ring closure was promoted by the ruthenium-based catalyst 10a or 10b. The resulting tetraresidue 11d was shown to undergo intramolecular hydrogen bonding based on NMR and FT-IR studies. Thus, the development of dehydro-Freidinger lactams as potential reverse turn inducers stabilizing an intramolecular NHi+3...COi hydrogen-bond was demonstrated.

"One-pot" methylation of N-nosyl-α-amino acid methyl esters with diazomethane and their coupling to prepare N-methyl dipeptides

N-Nosyl-α-amino acid methyl esters are methylated quantitatively with diazomethane. After proper deprotection of the amino function by treatment with the reagent system mercaptoacetic acid/sodium methoxide, the obtained N-methyl amino acid methyl esters are coupled with N-Fmoe amino acid chlorides to afford the corresponding dipeptides. The obtained products do not show any detectable extent of racemization by 1H NMR and HPLC.

Short and efficient synthesis of Homo-Freidinger lactams: An olefin metathesis approach towards conformationally restricted β-amino acid analogues

Peptide coupling of the N-allyl or N-homoallyl α-amino acid esters 6a-d with enantiomerically pure β-C-allylglycine gave access to the dienes 7a-d which were subjected to an olefin metathesis reaction. Thus, the novel lactam bridged peptide mimics 8a-d we