91028-39-6Relevant academic research and scientific papers
Radical-Mediated Acyl Thiol-Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives
Lynch, Dylan M.,McLean, Joshua T.,McSweeney, Lauren,Milbeo, Pierre,Scanlan, Eoin M.
supporting information, p. 4148 - 4160 (2021/08/24)
The thiol-ene ‘click’ reaction has emerged as a versatile process for carbon–sulfur bond formation with widespread applications in chemical biology, medicinal chemistry and materials science. Thioesters are key intermediates in a wide range of synthetic and biological processes and efficient methods for their synthesis are of considerable interest. Herein, we report the first examples of acyl-thiol-ene (ATE) for the synthesis of biomolecular thioesters, including peptide, lipid and carbohydrate derivatives. A key finding is the profound effect of the amino acid side chain on the outcome of the ATE reaction. Furthermore, radical generated thioesters underwent efficient S-to-N acyl transfer and desulfurisation to furnish ‘sulfur-free’ ligation products in an overall amidation process with diverse applications for chemical ligation and bioconjugation.
Cross-metathesis of C-allyl iminosugars with alkenyl oxazolidines as a key step in the synthesis of C-iminoglycosyl α-amino acids. A route to iminosugar containing C-glycopeptides
Dondoni, Alessandro,Giovannini, Pier Paolo,Perrone, Daniela
, p. 5508 - 5518 (2007/10/03)
A general access to a novel class of sugar α-amino acids composed of iminofuranose and iminopyranose residues anomerically linked to the glycinyl group through an alkyl chain is described. A set of eight compounds was prepared by the same reaction sequenc
Following an ISES lead: The first examples of asymmetric Ni(0)-mediated allylic amination
Berkowitz, David B.,Maiti, Gourhari
, p. 2661 - 2664 (2007/10/03)
An ISES (in situ enzymatic screening) lead pointed to conditions (PMP N-protecting group, Ni(cod)2 catalyst precursor) under which chiral, bidentate phosphines could promote Ni(0)-mediated allylic amination. Therefore, bidentate phosphines bear
Synthesis of unusual amino acids: N-(tert-butoxycarbonyl)-L-vinyl glycine and N-(tert-butoxycarbonyl)-L-homophenylalanine
Chandrasekhar,Raza, Abbas,Takhi, Mohamed
, p. 423 - 428 (2007/10/03)
The synthesis of the unusual amino acids N-(tert-butoxycarbonyl)-L-vinyl glycine and N-(tert-butoxycarbonyl)-L-homophenylalanine starting from commercially available D-xylose via an alkylative fragmentation method is described.
A convenient synthesis of L-α-vinylglycine from D-mannitol
Badorrey, Ramon,Cativiela, Carlos,Diaz-de-Villegas, Maria D.,Galvez, Jose A.
, p. 747 - 749 (2007/10/03)
A novel procedure is described for the synthesis of L-α-vinylglycine based on the diastereoselective addition of vinylmagnesium bromide to the N- benzyl imine derived from 2,3-O-isopropylidene-D-glyceraldehyde. The route developed is both convenient (only
On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding
Marcovici-Mizrahi, Dana,Gottlieb, Hugo E.,Marks, Vered,Nudelman, Abraham
, p. 8402 - 8406 (2007/10/03)
The syn-rotamers of carbamate derivatives of α-amino acids are shown to be stabilized by the formation of H-bond complexes with carboxylic acid moieties in solution. This effect is, as expected, concentration and temperature dependent. Thermodynamic parameters (both ΔG° and ΔG?) for N-Boc-alanine were determined by NMR in the ±60 °C range.
L-Vinylglycine
Afzali-Ardakani, Ali,Rapoport, Henry
, p. 4817 - 4820 (2007/10/02)
Optically pure L-vinylglycine (1) has been synthesized from L-methionine in 54percent overall yield.The process consists in first preparing N-methionine methyl ester (9) which is then oxidized to methyl 2-amino>-
