The efficient synthesis and simple resolution of a prolineboronate ester suitable for enzyme-inhibition studies

Kelly, Terence A.; Fuchs, V.; Perry, Clark W.; Snow, Roger J.

doi:10.1016/s0040-4020(01)86281-5

Cited by 45 publications

(38 citation statements)

References 25 publications

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“…Subsequent structural studies determined the instability to be due to intramolecular cyclization of the compound through formation of a B-N bond. The group showed that the ability to inhibit dipeptidyl peptidase IV relies on an equilibrium formed between both conformations [129,130]. The same group have performed SAR analysis with the aim of improving the biological activity of these compounds [131].…”

Section: Peptidyl Boronic Acidsmentioning

confidence: 99%

Strategies for the inhibition of serine proteases

Walker¹,

Lynas²

2001

CMLS, Cell. Mol. Life Sci.

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Serine proteases have been shown to play a multifarious role in health and disease. As a result, there has been considerable interest in the design and development of synthetic inhibitors of these enzymes. In view of their diverse roles in biological processing events, one of the great challenges in such endeavours has been the need to produce compounds with exquisite selectivity. Inhibitor design has been broadly guided by the use of either peptide- or heterocyclic-based compounds, designed to exploit the known substrate specificity characteristics of individual enzymes. This review describes the thinking and strategies employed in such efforts.

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Section: Peptidyl Boronic Acidsmentioning

confidence: 99%

Strategies for the inhibition of serine proteases

Walker¹,

Lynas²

2001

CMLS, Cell. Mol. Life Sci.

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“…The heterogeneous nature of this catalyst, which was confirmed by various mechanistic and spectroscopic experiments, is likely crucial to both the reactivity and selectivity of this system . To date, the hydrogenation of borylated arenes has been underexplored . Given the synthetic value of organoboron compounds and the fact that no general method for the construction of borylated carbo‐ and heterocycles is known, we believed that a thorough synthetic study was required.…”

Section: Methodsmentioning

confidence: 99%

Hydrogenation of Borylated Arenes

2018

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A cis‐selective hydrogenation of abundant aryl boronic acids and their derivatives catalyzed by rhodium cyclic (alkyl)(amino)carbene (Rh–CAAC) is reported. The reaction tolerates a variety of boron‐protecting groups and provides direct access to a broad scope of saturated, borylated carbo‐ and heterocycles with various functional groups. The transformation is strategically important because the versatile saturated boronate products are difficult to prepare by other methods. The utility of the saturated cyclic building blocks was demonstrated by post‐functionalization of the boron group.

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“…Die heterogene Natur dieses Katalysators, die durch verschiedene mechanistische und spektroskopische Experimente bestätigt wurde, ist wahrscheinlich sowohl für die Reaktivität, als auch für die Selektivität dieses Systems von entscheidender Bedeutung . Die Hydrierung borylierter Aromaten ist heute noch weitgehend unerschlossen . Angesichts der synthetischen Nützlichkeit von Organoborverbindungen und der Tatsache, dass bisher keine allgemeine Methode für den Aufbau von borylierten Carbo‐ und Heterocyclen bekannt ist, hielten wir eine umfassende Synthesestudie für erforderlich.…”

Section: Methodsunclassified

Hydrierung borylierter Aromaten

2018

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Die Rh‐CAAC‐katalysierte cis‐selektive Hydrierung von leicht verfügbaren aromatischen Boronsäuren und derer Derivate wird gezeigt. Die Reaktion toleriert verschiedene Bor‐Schutzgruppen und liefert direkten Zugang zu einem breiten Spektrum gesättigter, borylierter Carbo‐ und Heterocyclen mit verschiedenen funktionellen Gruppen. Die Transformation ist strategisch wichtig, da die vielseitig einsetzbaren gesättigten Boronate mit anderen Methoden nur schwer herzustellen sind. Die Anwendbarkeit der gesättigten, cyclischen Synthesebausteine wurde durch Post‐Funktionalisierung der Borgruppe demonstriert.

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The efficient synthesis and simple resolution of a prolineboronate ester suitable for enzyme-inhibition studies

Cited by 45 publications

References 25 publications

Strategies for the inhibition of serine proteases

Strategies for the inhibition of serine proteases

Hydrogenation of Borylated Arenes

Hydrierung borylierter Aromaten

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