219864-03-6Relevant academic research and scientific papers
ANTI-CD98 ANTIBODIES AND ANTIBODY DRUG CONJUGATES
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, (2018/01/15)
The invention relates to anti-CD98 antibodies and antibody drug conjugates (ADCs), including compositions and methods of using said antibodies and ADCs.
MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
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Page/Page column 82-83, (2014/07/08)
The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula (I). The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.
Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol
Zeng, Jing,Vedachalam, Seenuvasan,Xiang, Shaohua,Liu, Xue-Wei
, p. 42 - 45 (2011/03/22)
A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF3?Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.
Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues
Nishikawa, Toshio,Koide, Yuya,Kajii, Shigeo,Wada, Kyoko,Ishikawa, Miyuki,Isobe, Minoru
, p. 687 - 700 (2007/10/03)
The total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available α-methyl-D-mannoside in 10 steps including the following key steps: the C-glycosidation of a mannose derivative with a stannylacetylene, Castro indole synthesis, and Sc(ClO4)3-promoted coupling with L-serine-derived aziridine carboxylate. The glucose- and galactose-analogues of C-Man-Trp were also synthesized in a similar manner. Conformational analyses of the synthesized C-glycosyltryptophan and its synthetic intermediate are briefly discussed.
Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling
Dondoni, Alessandro,Mariotti, Giandomenico,Marra, Alberto
, p. 4475 - 4486 (2007/10/03)
A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of α- or β-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-α-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of α- and β-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.
Novel type of rigid C-linked glycosylacetylene-phenylalanine building blocks for combinatorial synthesis of C-linked glycopeptides
Lowary, Todd,Meldal, Morten,Helmboldt, Arnim,Vasella, Andrea,Bock, Klaus
, p. 9657 - 9668 (2007/10/03)
C-linked 3- and 4-(glycosylacetylene)-Fmoc-phenylalanines were synthesized as rigid building blocks for synthesis of libraries of neoglycopeptide templates. Perbenzylated 1,5-galactonolactone, 1,5- gluconolactone, and 1,5-mannonolactone were reacted with cerium TMS-acetylide and the products reduced to the C-glycosylacetylene-TMS derivatives. The gluco and galacto configurations yielded exclusively the β-C-glycoside, whereas the mannonolactone gave a mixture of α-C- and β-C-anomer. The products were subjected to acetolysis and TMS cleavage. The resulting peracetylated glycosylacetylenes were cross-coupled with the (R,S)-N(α)- acetyl-3- and 4-iodophenylalanine O-methyl esters by Pd(0) catalysis in piperidine to give the eight possible C-linked glycosyl amino acid building blocks 33-40 as diastereomeric pairs. These were O-deacetylated. As an example of further conversion into neoglycopeptide templates the N-acetyl group of the 4-linked galacto-diastereomeric pair 43 was hydrolyzed selectively by acylase 1 and separated from the (R)stereoisomer. The product was converted to 4-(β-C-galactosylacetylene)(N(α)-Fmoc-)-L-phenylalanine (52) by reaction with Fmoc-OSu. Acid hydrolysis of galactosyl acetylene phenyl alanine 43 at elevated temperature afforded the conversion of the acetylene to the 1'-oxo derivative which was also N(α)-Fmoc protected. The building blocks were used in the glycopeptide synthesis of three neoglycopeptide templates 54, 55, and 56 known to bind to murine MHC class II E(k) and to present the glycan for interaction with the T-cell receptor. This template has previously been employed to elicit a carbohydrate specific T- cell response.
