55378-79-5Relevant articles and documents
Complexation of anions including nucleotide anions by open-chain host compounds with amide, urea, and aryl functions
Werner, Frank,Schneider, Hans-Joerg
, p. 465 - 478 (2000)
A systematical evaluation of association constants between halide, phosphate, and carboxylate anions with N-methylformamide (1) and the related bidentate receptors 2-6 (derived from, e.g., phthalic acid or ethylenediamine) in CDCl3 as solvent y
Synthesis of Nα-Z protected amino alkyl triazole acids and their application to neo-glycopeptides synthesis
Madhu, Chilakapati,Panguluri, Nageswara Rao,Sureshbabu, Vommina V.
, p. 858 - 864 (2014/08/05)
The synthesis of triazole linked glycopeptides employing 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) mediated coupling of Z-protected triazole acids with glycosyl amines and amino acid esters is described. The coupling proceeded smoothly at room temperat
One-pot synthesis of orthogonally protected dipeptide selenazoles employing Nα-amino selenocarboxamides and α-bromomethyl ketones
Madhu, Chilakapati,Panguluri, Nageswara Rao,Narendra,Panduranga,Sureshbabu, Vommina V.
supporting information, p. 6831 - 6835 (2015/01/09)
A simple and efficient protocol for the synthesis of selenazole containing dipeptidomimetics using Nα-amino selenocarboxamides and α-bromomethyl ketones is described. All the compounds made were isolated in good yields and fully characterized.
Direct synthesis of phosphinopeptides containing C-terminal α-aminoalkylphosphinic acids
Meng, Fanhua,Xu, Jiaxi
experimental part, p. 533 - 538 (2010/11/04)
A series of phosphinopeptides containing C-terminal α- aminoalkylphosphinic acids were prepared in good yields directly in one-pot reactions of 2-(N-benzoxycarbonylamino)alkanamides/peptide amides, aldehydes, and aryldichlorophosphines, followed by hydrolysis. In the current method, the peptide bond was formed in a Mannichtype reaction. Springer-Verlag 2010.
Serine and threonine β-lactones: A new class of hepatitis A virus 3C cysteine proteinase inhibitors
Lall, Manjinder S.,Ramtohul, Yeeman K.,James, Michael N.G.,Vederas, John C.
, p. 1536 - 1547 (2007/10/03)
Hepatitis A virus (HAV) 3C enzyme is a cysteine proteinase essential for viral replication and infectivity and represents a target for the development of antiviral drugs. A number of serine and threonine β-lactones were synthesized and tested against HAV 3C proteinase. The D-N-Cbz-serine β-lactone 5a displays competitive reversible inhibition with a Ki value of 1.50 × 10-6 M. Its enantiomer, L-N-Cbz-serine β-lactone 5b is an irreversible inactivator with kinact = 0.70 min-1, KI = 1.84 × 10-4 M and kinact/KI = 3800 M-1 min-1. Mass spectrometry and HMQC NMR studies using 13C-labeled 5b show that inactivation of the enzyme occurs by nucleophilic attack of the cysteine thiol (Cys-172) at the β-position of the oxetanone ring. Although the N-Cbz-serine β-lactones 5a and 5b display potent inhibition, other related analogues with an N-Cbz side chain, such as the five-membered ring homoserine γ-lactones 14a and 14b, the four-membered ring β-lactam 33, 2-methylene oxetane 34, cyclobutanone 36, and 3-azetidinone 39, fail to give significant inhibition of HAV 3C proteinase, thus demonstrating the importance of the β-lactone ring for binding.
Carbopeptoids: Peptides and diketopiperazines incorporating the anomeric centre of mannopyranose
Long, Daniel D.,Tennant-Eyles, Richard J.,Estevez, Juan C.,Wormald, Mark R.,Dwek, Raymond A.,Smith, Martin D.,Fleet, George W.J.
, p. 807 - 813 (2007/10/03)
An approach to the synthesis of D-mannopyranose derivatives incorporating an anomeric α-amino acid component is described. An N-acylated bicyclic [2.2.2] lactone, formed via an oxidative ring closure, provides access to a new class of glycopeptide analogues of D-mannopyranose and determines the anomeric configuration of compounds derived therefrom. The mannopyranose diketopiperazine may be equilibrated to the more stable furanose form under basic conditions; in general, mannopyranose derivatives containing an α-amino acid moiety at the anomeric position are less stable than the mannofuranose isomers.
Syntheses of peptidoglycolipid analogs with distinct immunomodulating activities
Lockhoff, Oswald,Hayauchi, Yutaka
, p. 603 - 619 (2007/10/03)
Amphiphilic 2-amino-2-deoxy-β-D-glucopyranosylamides were synthesized from N-protected glucosamine derivatives via N-glycosidation with fatty amines, subsequent N-acylation with fatty acid derivatives and deprotection. They could further be modified with
Synthesis of functionalised oxazoles and bis-oxazoles
Bagley, Mark C.,Buck, Richard T.,Hind, S. Lucy,Moody, Christopher J.
, p. 591 - 600 (2007/10/03)
A new method for the synthesis of oxazoles, and in particular chiral non-racemic oxazoles derived from amino acids, has been developed. Thus, rhodium(II) catalysed reaction of diazocarbonyl compounds 6 and 11 in the presence of amides 8 and 10 results in regioselective insertion of the carbenoid into the amide N-H bond with formation of the β-carbonyl amides 9 and 12. Cyclodehydration of amides 9 and 12 using triphenylphosphine-iodine-triethylamine gives functionalised oxazoles 7 and 13. The oxazoles 13c and 13f were converted into the bis-oxazoles 17a and 17b by a second rhodium(II) catalysed regioselective N-H insertion reaction on the amides 15, followed by cyclodehydration.
Spirodiketopiperazines of mannofuranose: Carbopeptoid α-amino acid esters at the anomeric position of mannofuranose
Estevez, Juan C.,Burton, Jonathan W.,Estevez, Ramon J.,Ardron, Helen,Wormald, Mark R.,Dwek, Raymond A.,Brown, David,Fleet, George W.J.
, p. 2137 - 2154 (2007/10/03)
Epimeric mannofuranose anomeric aminoesters are prepared from readily available azidolactones and can act as building blocks for the incorporation of mannofuranose units into peptide chains [carbopeptoids]; alternative acylating conditions allow either ra
Mimics of L-rhamnose: Anomeric spirohydantoins and diketopiperazines - Approaches to novel N-linked glycopeptides of rhamnofuranose
Estevez, Juan C.,Smith, Martin D.,Lane, Alexandra L.,Crook, Sarah,Watkin, David J.,Besra, Gurdyal S.,Brennan, Patrick J.,Nash, Robert J.,Fleet, George W. J.
, p. 387 - 390 (2007/10/03)
An α-azidocarboxylate of a tetrahydrofuran derived from L-rhamnose may be used as a divergent intermediate for a wide range of mimics of L-rhamnofuranose, which contain a constituent α-amino acid moiety at the anomeric position, and include anomeric spiro
