171978-60-2

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 66866-44-2 Boc-Leu-O-COO-isoBu 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 200937-21-9 N-tert-butoxycarbonyl-L-leucine monohydrate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 15136-32-0 (N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 61-90-5 L-leucine 

Downstream Products

• 1414493-21-2 tert-butyl (2S,3S,6S)-3-benzyl-2-(iodomethyl)-6-isobutyl-5-oxopiperazine-1-carboxylate 

Relevant academic research and scientific papers

Synthesis of the Nonribosomal Peptide Phevalin and Analogs

Phevalin, a cyclic nonribosomal peptide produced by Staphylococcus aureus, has intriguing biological properties. A synthetic route to access phevalin and similar pyrazinone natural products tyrvalin, leuvalin, phileucin, and a few synthetic analogs is described. The reaction sequence involves a one-pot carbamate deprotection/imine formation/aerobic oxidation to form the pyrazinone-containing products.

The role of N-terminal heterocycles in hydrogen bonding to α-chymotrypsin

A series of dipeptide aldehydes containing different N-terminal heterocycles was prepared and assayed in vitro against α-chymotrypsin to ascertain the importance of the heterocycle in maintaining a β-strand geometry while also providing a hydrogen bond do

An efficient entry to highly substituted chiral 2-oxopiperazines from α-amino acids via iodocyclization

A short and stereoselective route for the synthesis of 2-oxopiperazines is presented starting from different naturally abundant α-amino acids. The key synthetic steps involved amide coupling, Wittig reaction, HWE olefination, aza-Michael reaction, iodocyc

Employing the structural diversity of nature: Development of modular dipeptide-analogue ligands for ruthenium-catalyzed enantioselective transfer hydrogenation of ketones

A library of novel dipeptideanalogue ligands based on the combination of tert-butoxycarbonyl(N-Boc)-protected a-amino acids and chiral vicinal amino alcohols were prepared. These highly modular ligands were combined with [{RuCl2(p-cymene)}2 and the resulting metal complexes were screened as catalysts for the enantioselective reduction of acetophenone under transfer hydrogenation conditions using 2-propanol as the hydrogen donor. Excellent enantioselectivity of 1-phenylethanol (up to 98% ee) was achieved with several of the novel catalysts. Although most of the ligands contained two stereocenters, it was demonstrated that the absolute configuration of the product alcohol was determined by the configuration of the amino acid part of the ligand. Employing ligands based on L-amino acids generated S-configured products, and catalysts based on Damino acids favored the formation of the R-configured alcohol. The combination N-Boc-L-alanine and (R)-phenylglycinol (Boc-L-Ab) or its enantiomer (N-Boc-D-alanine and (S)-phenylglycinol, Boc-D-Aa) proved to be the best ligands for the reduction process. Transfer hydrogenation of a number of aryl alkyl ketones were evaluated and excellent enantioselectivity, up to 96 % ee, was obtained.

Chemotactic peptide analogues: Synthesis and chemotactic activity of N-formyl-Met-Leu-Phe analogues containing (S)-phenylalaninol derivatives

The synthesis and the biological activity towards human neutrophils of some N-formyl-Met-Leu-Phe-OMe analogues containing (S)-phenylalaninol (Pheol) or its derivatives in place of the native phenylalanine are reported. While the analogue containing Pheol (4) was found to be devoid of significant biological activity, its ester 3 and 5, although inactive as chemoattractants, are able to strongly stimulate superoxide production and are active with a lower efficacy in the lysozyme release.