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Mark Von Itzstein - One of the best experts on this subject based on the ideXlab platform.
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Access to 3-O-Functionalized N-Acetylneuraminic Acid Scaffolds.
The Journal of organic chemistry, 2015Co-Authors: Mauro Pascolutti, Paul D. Madge, Robin J. Thomson, Mark Von ItzsteinAbstract:Direct access to 3-O-functionalized 2-α-N-acetylneuraminides and their corresponding 2,3-dehydro-2-deoxy-N-Acetylneuraminic Acid derivatives is described. Initially, a stereoselective ring-opening of the key intermediate N-Acetylneuraminic Acid (Neu5Ac) 2,3-β-epoxide with an alcohol provided the 3-hydroxy α-glycoside. O-Alkylation of the C3 hydroxyl group generated novel 3-O-functionalized Neu5Ac derivatives that provided the corresponding unsaturated derivatives upon elimination.
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Synthesis and evaluation of C-9 modified N-Acetylneuraminic Acid derivatives as substrates for N-Acetylneuraminic Acid aldolase
Bioorganic & medicinal chemistry, 2000Co-Authors: Milton J Kiefel, Jennifer C. Wilson, Simon Bennett, Matt Gredley, Mark Von ItzsteinAbstract:Several C-9 modified N-Acetylneuraminic Acid derivatives have been synthesised and evaluated as substrates of N-Acetylneuraminic Acid aldolase. Simple C-9 acyl or ether modified derivatives of N-Acetylneuraminic Acid were found to be accepted as substrates by the enzyme, albeit being transformed more slowly than Neu5Ac itself. 1H NMR spectroscopy was used to evaluate the extent of the enzyme catalysed transformation of these compounds. Interestingly, the chain-extended Neu5Ac derivative 16 Figure FX4. Figure options Download full-size image Download high-quality image (23 K) Download as PowerPoint slide is not a substrate for N-acetylneuraminate lyase and behaves as an inhibitor of the enzyme.
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Synthesis of C11 chain-extended analogues of N-Acetylneuraminic Acid
Journal of the Chemical Society Perkin Transactions 1, 1996Co-Authors: Milton J Kiefel, Simon M. W. Bennett, Mark Von ItzsteinAbstract:The synthesis of novel C11 chain-extended analogues of N-Acetylneuraminic Acid has been achieved from the N-acetyl-9-hydroxyneuraminic Acid derivative 7 via a Swern oxidation/Wittig olefination sequence. In this way the novel α,β-unsaturated ester 12, the saturated ester 13 and the α,β-unsaturated aldehyde 14 of N-Acetylneuraminic Acid have been prepared in good overall yield.
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Synthesis of C-4-disubstituted analogues of N-Acetylneuraminic Acid
Journal of the Chemical Society Perkin Transactions 1, 1996Co-Authors: Darrin R. Groves, Mark Von ItzsteinAbstract:The synthesis of some novel C-4-disubstituted analogues of N-Acetylneuraminic Acid has been achieved by nucleophilic opening of the epoxide ring in the acetyl-4,4′-anhydroneuraminic Acid derivatives 6 and 7. This has provided the azide 8, the methyl ether 9, the nitrile 10 and the chloride 11 of the 8,9-isopropylidenated β-methyl ketoside of methyl N-acetylneuraminate in moderate to good yields.
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The first synthesis of an alkylmercury containing N-Acetylneuraminic Acid derivative
Tetrahedron Letters, 1996Co-Authors: Milton J Kiefel, Mark Von ItzsteinAbstract:Abstract Structurally modified N -acetylneuraminic Acids are important as potential substrates or inhibitors of sialic Acid-recognising proteins as well as probes for the elucidation of sialic Acid metabolism. This report describes the synthesis of a novel alkylmercury-containing N -acetylneuraminic Acid derivative as a potential heavy-atom derivative for use in X-ray crystallographic studies.
Joo-hack Youn - One of the best experts on this subject based on the ideXlab platform.
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Asymmetric synthesis of N-Acetylneuraminic Acid
Chemical Communications, 2000Co-Authors: Sung Ho Kang, Choi Hyeong-wook, Joon Kim, Joo-hack YounAbstract:A highly diastereoselective synthesis of N-Acetylneuraminic Acid 1 has been completed by stereoselective functionalization of cis-olefin 6 and trans-olefin 10 via intramolecular phenylselenoamidation and osmylation, respectively.
Sung Ho Kang - One of the best experts on this subject based on the ideXlab platform.
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Asymmetric synthesis of N-Acetylneuraminic Acid
Chemical Communications, 2000Co-Authors: Sung Ho Kang, Choi Hyeong-wook, Joon Kim, Joo-hack YounAbstract:A highly diastereoselective synthesis of N-Acetylneuraminic Acid 1 has been completed by stereoselective functionalization of cis-olefin 6 and trans-olefin 10 via intramolecular phenylselenoamidation and osmylation, respectively.
Milton J Kiefel - One of the best experts on this subject based on the ideXlab platform.
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Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N-Acetylneuraminic Acid
Journal of Organic Chemistry, 2016Co-Authors: James T Williams, Leo Corcilius, Milton J Kiefel, Richard J. PayneAbstract:The pseudaminic Acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic Acids that are functional components of flagellin and pili proteins within clinically relevant Gram-negative bacteria. Herein, we describe the total synthesis of the most common pseudaminic Acid, 5,7-diacetylpseudaminic Acid, from N-Acetylneuraminic Acid. The divergent nature of the route reported here provides a robust and versatile means to access other members of the family, together with analogues, for probing the functional role of the pseudaminic Acids and pseudaminic Acid derived proteins in the future.
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Synthesis and evaluation of C-9 modified N-Acetylneuraminic Acid derivatives as substrates for N-Acetylneuraminic Acid aldolase
Bioorganic & medicinal chemistry, 2000Co-Authors: Milton J Kiefel, Jennifer C. Wilson, Simon Bennett, Matt Gredley, Mark Von ItzsteinAbstract:Several C-9 modified N-Acetylneuraminic Acid derivatives have been synthesised and evaluated as substrates of N-Acetylneuraminic Acid aldolase. Simple C-9 acyl or ether modified derivatives of N-Acetylneuraminic Acid were found to be accepted as substrates by the enzyme, albeit being transformed more slowly than Neu5Ac itself. 1H NMR spectroscopy was used to evaluate the extent of the enzyme catalysed transformation of these compounds. Interestingly, the chain-extended Neu5Ac derivative 16 Figure FX4. Figure options Download full-size image Download high-quality image (23 K) Download as PowerPoint slide is not a substrate for N-acetylneuraminate lyase and behaves as an inhibitor of the enzyme.
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Synthesis of C11 chain-extended analogues of N-Acetylneuraminic Acid
Journal of the Chemical Society Perkin Transactions 1, 1996Co-Authors: Milton J Kiefel, Simon M. W. Bennett, Mark Von ItzsteinAbstract:The synthesis of novel C11 chain-extended analogues of N-Acetylneuraminic Acid has been achieved from the N-acetyl-9-hydroxyneuraminic Acid derivative 7 via a Swern oxidation/Wittig olefination sequence. In this way the novel α,β-unsaturated ester 12, the saturated ester 13 and the α,β-unsaturated aldehyde 14 of N-Acetylneuraminic Acid have been prepared in good overall yield.
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The first synthesis of an alkylmercury containing N-Acetylneuraminic Acid derivative
Tetrahedron Letters, 1996Co-Authors: Milton J Kiefel, Mark Von ItzsteinAbstract:Abstract Structurally modified N -acetylneuraminic Acids are important as potential substrates or inhibitors of sialic Acid-recognising proteins as well as probes for the elucidation of sialic Acid metabolism. This report describes the synthesis of a novel alkylmercury-containing N -acetylneuraminic Acid derivative as a potential heavy-atom derivative for use in X-ray crystallographic studies.
Choi Hyeong-wook - One of the best experts on this subject based on the ideXlab platform.
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Asymmetric synthesis of N-Acetylneuraminic Acid
Chemical Communications, 2000Co-Authors: Sung Ho Kang, Choi Hyeong-wook, Joon Kim, Joo-hack YounAbstract:A highly diastereoselective synthesis of N-Acetylneuraminic Acid 1 has been completed by stereoselective functionalization of cis-olefin 6 and trans-olefin 10 via intramolecular phenylselenoamidation and osmylation, respectively.
