18939-41-8

Upstream product

• 16069-16-2 N-(acryloyl)-L-phenylalanine 
• 16045-88-8 boron trifluoride methanol complex 
• 63-91-2 L-phenylalanine 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 814-68-6 acryloyl chloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

Downstream Products

• 117835-12-8 N-acryloyl-L-phenylalanine isopropyl ester 
• 1632322-70-3 (S)-methyl 2-(3-(5-ethyl-1H-pyrrol-2-yl)propanamido)-3-phenylpropanoate 
• 1632322-69-0 (S)-methyl 2-(3-(3,5-dimethyl-1H-pyrrol-2-yl)propanamido)-3-phenylpropanoate 
• 1632322-68-9 (S)-methyl 2-(3-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)propanamido)-3-phenylpropanoate 
• 209622-29-7 (S)-2-[(1-Benzyloxycarbonylmethyl-aziridine-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

Controlled radical polymerization of an acrylamide containing L-phenylalanine moiety via RAFT

Homopolymers of a monosubstituted acrylamide having an amino acid moiety in the side chain, N-acryloyl-L-phenylalanine methyl ester (A-Phe-OMe), have been synthesized by reversible addition - fragmentation chain transfer (RAFT) polymerization. Two dithioe

Controlling Amphiphilic Polymer Folding beyond the Primary Structure with Protein-Mimetic Di(Phenylalanine)

While methods for polymer synthesis have proliferated, their functionality pales in comparison to natural biopolymers-strategies are limited for building the intricate network of noncovalent interactions necessary to elicit complex, protein-like functions

METALLOPROTEASE INHIBITORS, METHODS FOR PRODUCING SAME, AND THERAPEUTIC USES THEREOF

The invention relates to new α-vinyl carbonylated compounds corresponding to general formula (I), wherein R1, R2, R3, R4, R5 and Y are as defined in claim 1, their isomers, their diastereoisomers and

Studies of the new reactivity of chiral acrylamides and unprotected pyrroles: Diastereoselective and carbonyl compatible 1,4-addition

A diversity of new functionalized cyclic and acyclic chiral pyrroloamides compounds were synthesized in good yields and diastereoselectivities in the case of cyclic pyrroloamides. This simple and robust process involves the creation of a C-C bond between unprotected pyrroles and cyclic or hindered chiral acrylamides. Georg Thieme Verlag Stuttgart New York.

Studies in the synthesis and reactivity of new chiral 1-[(trialkylsilyl)- methyl]propenamides

A very simple sequence of reactions such as cross-·metathesis using two catalysts and allylation to give the chiral hydroxyamide is described.

Poly(n-acryl amino acids): A new class of biologically active polyanions

Poly(N-acryl amino acids) bearing side groups with a lipophilic character or having charged functional groups (i.e. -NH2, -COOH, -SH, -OH, and phenols) were synthesized from the radical polymerization of N-acryl amino acid monomers. Monomers were prepared from the reaction of acryloyl chloride and amino acid esters in dry solvents. Polymers of a broad molecular weight ranging from 3 000 to 60 000 Da were obtained. The polymers were optically active, and their structures were confirmed by 1H NMR and IR spectra and elemental analysis. Hydroxyl-containing polymers were sulfated in high conversion yields by SO3/pyridine complex. The newly synthesized linear homopolyanions were tested for heparin-like activities: (i) inhibition of heparanase enzyme, (ii) release of basic fibroblast growth factor (bFGF) from the extracellular matrix (ECM), and (iii) inhibition of smooth muscle cell (SMC) proliferation. Polymers based on tyrosine and leucine were highly active in all three tests (microgram level). Polymers based on phenylalanine, tert-leucine, and proline were active as heparanase inhibitors and FGF release, and polymers of trans-hydroxyproline, glycine, and serine were active only as heparanase inhibitors. The polymer of cis-hydroxyproline was inactive. It was found that a net anionic charge (i.e. carboxylic acid) is essential for biological activity. Thus, methyl ester derivatives of the active polymers, zwitterionic amino acid pendent groups (lysine, histidine), and decarboxylated amino acids (tyramine, ethanolamine) were inactive. The above active polymers did not exhibit anticoagulation activity which is considered the main limitation of heparin and heparinomimetics for clinical use. These synthetic poly(N-acryl amino acids) may have potential use in the inhibition of heparanase-mediated degradation of basement membranes associated with tumor metastasis, inflammation, and autoimmunity.

Small ring constrained pepfidomimetics. Synthesis of aziridine parallel β-sheet mimetics

The synthesis of a series of novel amino acids and peptides containing an aziridine ring is described. Their preparation is based on the Gabriel- Cromwell reaction of amino acids or peptides with different 2-bromo acrylates and acrylamides. These products are constituted by a turned scaffold (the aziridine) where two parallel peptidic strands can be grown to produce a β- sheet mimetic.

Models for Use of α-Amino Acids as Chiral Auxiliaries in Asymmetric Diels-Alder Reactions

Three different models, depending on the Lewis acid used as a catalyst and the α-amino acid used as a chiral auxiliary, account for the diastereofacial selectivity obtained in reactions of cyclopentadiene with N-acryloyl derivatives of L-proline, L-phenylalanine, L-alanine, and N-methyl-L-alanine esters.For α-amino acids without an NH group and aluminum catalysts, a reactive conformer with antiplanar enoate conformation similar to those postulated for acrylates with only one center capable of coordination is proposed.These dienophiles form a chelate complex, where the acryloyl moiety is in syn conformation, with TiCl4.For α-amino acids with an NH group, a reactive intermediate with an antiplanar disposition in the acryloyl moiety and the conformation of the amino ester fixed by an intramolecular hydrogen bond accounts for the results with both kinds of catalyst.These models seem to have general application for the use of α-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions.