80174-60-3

Upstream product

• 106-31-0 butanoic acid anhydride 
• 150-30-1 Phenylalanine 
• 63-91-2 L-phenylalanine 
• 107-92-6 butyric acid 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 623-42-7 butanoic acid methyl ester 
• 371-27-7 2,2,2-trifluoroethylbutyrate 

Relevant academic research and scientific papers

Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification

Genome mining of microbial natural products enables chemists not only to discover the bioactive molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate-forming enzyme that adenylates a unique building block, 3-isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile natural product SF2768 produced by Streptomyces thioluteus, and this AMP-ligase was demonstrated to accept a broad range of short-chain fatty acids (SCFAs). Herein, we repurpose SfaB to catalyze amidation or thioesterification between those SCFAs and various amine or thiol nucleophiles, thereby providing an alternative enzymatic approach to prepare the corresponding amides and thioesters in vitro.

Design, synthesis and docking studies of novel dipeptidyl boronic acid proteasome inhibitors constructed from αα- and αβ-amino acids

A series of novel dipeptidyl boronic acid proteasome inhibitors constructed from αα- and αβ-amino acids were designed and synthesized. Their structures were elucidated by 1H NMR, 13C NMR, LC-MS and HRMS. These compounds were evaluated for their β5 subunit inhibitory activities of human proteasome. The results showed that dipeptidyl boronic acid inhibitors composed of αα-amino acids were as active as bortezomib. Interestingly, the activities of those derived from αβ-amino acids lost completely. Of all the inhibitors, compound 22 (IC50 = 4.82 nM) was the most potent for the inhibition of proteasome activity. Compound 22 was also the most active against three MM cell lines with IC50 values less than 5 nM in inhibiting cell growth assays. Molecular docking studies displayed that 22 fitted very well in the β5 subunit active pocket of proteasome.

The non-metathetic role of Grubbs' carbene complexes: From hydrogen-free reduction of α,β-unsaturated alkenes to solid-supported sequential cross-metathesis/reduction

An efficient and high-yielding "hydrogen-free" reduction of α,β-unsaturated alkenes was carried out employing Grubbs' catalyst in a non-metathetic role and Et3SiH. Conditions were optimized under microwave irradiation. Application to the solid-phase organic synthesis allows a facile construction of sp3-sp3 carbon bonds through a sequential cross metathesis/olefin reduction.

Application of AlMe3-mediated amidation reactions to solution phase peptide synthesis

A practical modification of the Weinreb amidation protocol employing amino acids as the amine reaction partner has been developed that allows for the facile synthesis of oligopeptides in solution.

Use of compositions of matter containing N-acylates of alpha aminoacids for the treatment of skin

This invention relates to new compositions of matter for use in treating wrinkling of the human skin. The compositions comprise, as an essential ingredient therein, at least one N-acylate, by butyric acid, of an alpha-amino acid or a salt of said acylate with an inorganic, organic or biologic base or with a metal.

Resolution of N-acyl-DL (+)-phenylalanines

The treatment of N-acyl-DL(+)-phenylalanines with D(-)-2-(2,5-dimethylbenzylamino)-1-butanol results in the formation of the D(-)-2-(2,5-dimethylbenzylamino)-1-butanol salt which is obtained as a crystallizate of the N-acyl-L(+)-phenylalanine and from which the desired N-acyl-L(+)-phenylalanine, an intermediate useful for the preparation of artificial sweetening agents, can be recovered.