15028-44-1Relevant articles and documents
The enzyme-catalysed stereoselective transesterification of phenylalanine derivatives in supercritical carbon dioxide
Smallridge, Andrew J.,Trewhella, Maurie A.,Wang
, p. 259 - 262 (2002)
The subtilisin Carlsberg catalysed transesterification of N-acetyl phenylalanine methyl ester (1), N-acetyl phenylalanine ethyl ester (2), N-trifluoroacetyl phenylalanine methyl ester (3) and N-trifluoroacetyl phenylalanine ethyl ester (4) was studied in supercritical carbon dioxide. The water content of the reaction affects the reactivity of the system; for the transesterification of the methyl esters with ethanol the optimum concentration of water was determined to be about 0.74 M, while for the transesterification of the ethyl esters with methanol the optimum concentration of water was about 1.3 M. The conversion is also dependent upon the concentration of alcohol; for ethanol, 2% v/v gives the maximum conversion, whilst for methanol, only 0.8-1. 2% v/v is required. This is probably due to a difference in the solubility of the substrates in the two alcohol/supercritical carbon dioxide mixtures. The reaction is highly stereoselective, in all cases no evidence for reaction of the D-isomer could be detected by chiral gas chromatography.
Efficient lanthanide catalysis in aminoacyl-transfer from the bipyridine-functionalized amide-substrate to alcohols at ambient temperature
Araki, Koji,Kajikawa, Takeshi,Kawaguchi, Satoshi
, p. 295 - 296 (1996)
Lanthanide cations showed high catalytic activities in aminoacylation of alcohols by the amide-substrates having bipyridine as a metal chelation site at 30°C (first-order rate constants were 10-4 s-1 range at Ce3+/substrate = 0.2), yielding corresponding amino acid esters almost quantitatively.
Fluorinated diphenylalanine analogue based supergelators: a stencil that accentuates the sustained release of antineoplastic drugs
Tiwari, Priyanka,Gupta, Arindam,Mehra, Radha Rani,Khan, Naureen,Harjit, Jeena,Ashby, Charles R.,Basu, Anindya,Tiwari, Amit K.,Singh, Manju,Dutt Konar, Anita
, p. 495 - 507 (2020)
Inspired by the prolonged metabolism displayed by para substituted fluorinated drugs, we intended to design two isomers Fmoc-(4F)-Phe-Phe-OH (hydrogelator I) & Fmoc-(3F)-Phe-Phe-OH (hydrogelator II) to explore the propensity of fluorine substitution in the aromatic ring of phenylalanine, in assisting or disrupting the gelation phenomena. However, our experimental observation reveals that hydrogelator I and II containing fluorines in the aromatic core illustrates excellent hydrogelation ability in comparison to the unsubstituted analogue, in accordance with the computational findings. Indeed, the hydrogelators displayed b-sheet with a fibrillar tape like morphology and were found to be biocompatible. We developed hydrogel nanoparticles (HNPs) that exhibited particle size less than 200 nm, and were found to release the antineoplastic drugs, 5Fluorouracil, curcumin and doxorubicin in a sustained manner depending on the architectural parameters of the drugs. Thus the prospective use of these compounds holds immense promise as a potential tool for future drug delivery applications.
Belikov et al.
, (1977)
Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts
Kervefors, Gabriella,Kersting, Leonard,Olofsson, Berit
, p. 5790 - 5795 (2021/03/08)
A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.
Synthesis and Penicillin-binding Protein Inhibitory Assessment of Dipeptidic 4-Phenyl-β-lactams from α-Amino Acid-derived Imines
Decuyper, Lena,Juki?, Marko,Sosi?, Izidor,Amoroso, Ana Maria,Verlaine, Olivier,Joris, Bernard,Gobec, Stanislav,D'hooghe, Matthias
, p. 51 - 55 (2019/11/28)
Monocyclic β-lactams revive the research field on antibiotics, which are threatened by the emergence of resistant bacteria. A six-step synthetic route was developed, providing easy access to new 3-amino-1-carboxymethyl-4-phenyl-β-lactams, of which the penicillin-binding protein (PBP) inhibitory potency was demonstrated biochemically.
