Solid phase synthesis – designer linkers for combinatorial chemistry: a review

Gordon, Kirsteen; Balasubramanian, Shankar

doi:10.1002/(sici)1097-4660(199909)74:9<835::aid-jctb130>3.3.co;2-q

Cited by 15 publications

(19 citation statements)

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“…This section will not attempt to replicate these, but rather illustrate the evolution of the concept of the diversity linker unit. [2,3,[9][10][11][12][13][14][15][16][17] Reflecting their genesis in solid-phase peptide and oligonucleotide synthesis, early linker units typically possessed a polar functional group (e.g. OH, NH 2 , CO 2 H, etc.)…”

Section: Linker Cleavage Strategies: An Overviewmentioning

confidence: 99%

Diversity Linker Units for Solid‐Phase Organic Synthesis

Scott

Steel

2006

Eur J Org Chem

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In recent years an ever‐increasing number of traditional solution‐phase reactions have been adapted for solid‐phase organic synthesis (SPOS) because of the ease of application of solid‐phase techniques to combinatorial chemistry and high‐throughput screening. To accommodate the growing number of reactions being attempted on solid supports, new linker units continue to be reported in the literature. Linker units are typically grouped according to the functionality left at the “cleavage site” in the target molecule, and are normally classified as traditional (polar functionality remains following cleavage) or traceless (hydrogen residue left after cleavage) linkers. As the field continues to expand, however, more advanced linker units have been reported, which utilise the cleavage step in SPOS to incorporate additional diversity into target libraries. These linker units have been termed “diversity” or “multifunctional” linker units, and in this microreview we introduce this aspect of the field, giving representative examples indicating key stages of development including the linker units recently designed in our laboratory. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Linker Cleavage Strategies: An Overviewmentioning

confidence: 99%

Diversity Linker Units for Solid‐Phase Organic Synthesis

Scott

Steel

2006

Eur J Org Chem

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“…Previously, linkers have mostly been cleaved by classical chemical methods, for instance, using strong acids. [1] Such conditions often restrict the application of linkers. Acid-sensitive linkers are not suitable for acid-labile compounds, such as carbohydrates.…”

Section: Abstract: Hydrazine; Hydrolysis; Penicillin G Amidase; Phenymentioning

confidence: 99%

Penicillin G Amidase‐Catalysed Hydrolysis of Phenylacetic Hydrazides on a Solid Phase: A New Route to Enzyme‐Cleavable Linkers

et al. 2005

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A novel catalytic property of penicillin G amidase (PGA) is described. Unexpectedly, the enzyme can hydrolyse hydrazide bonds with good efficiency, and in solution the enzyme shows a selectivity that is similar to phenylacetamides. The hydrolysis of phenylacetic hydrazides releases hydrazine, but no inhibition due to the formation of such reactive compounds was observed. This novel catalytic property was assayed also on a solid phase as a pioneering route for the design of enzyme-cleavable linkers and masked scavengers for ketones. On a solid phase a phenylacetic hydrazide compound was chemically synthesised on PEGA 1900 and PEGA þ (two co-polymers of acrylamide and ethylene glycol) and the efficiency of PGA in the release of phenylacetic acid depended on the diffusion of the protein inside the polymer. On PEGA þ the enzyme, as previously described, shows a good diffusion due to an improved electrostatic interaction with PGA thus achieving good hydrolytic conversions.

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“…Auch Gruppen, die im Abspaltungsschritt intermolekular reagieren, bleiben gebunden 260. Häufig wird im cyclisierenden Schritt eine C‐Heteroatom‐Bindung gebildet, aber auch Beispiele für C‐C‐Verknüpfungen sind bekannt 261…”

Section: Polymergestützte Trenn‐ Und Reinigungsverfahrenunclassified

“…Als Vorzüge dieser Methode sind zu nennen: die chemische Stabilität olefinischer Linker, die milden Spaltungsbedingungen und die Kompatibilität des Katalysators mit funktionellen Gruppen (z. B. mit ‐COOH, ‐CONH‐, ‐CHO, ‐CO‐, ‐OH, ‐SONH‐) 261…”

Section: Polymergestützte Trenn‐ Und Reinigungsverfahrenunclassified

Moderne Trennverfahren zur effizienten Aufarbeitung in der organischen Synthese

et al. 2002

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Die kombinatorische Synthese [1,2] wird als eine der Schl¸s-seldisziplinen f¸r den konstanten Nachschub an chemischen Verbindungen angesehen, die auf biologische Aktivit‰t gegen¸ber der immens wachsenden Zahl biologischer Zielmolek¸le getestet werden kˆnnen. Zusammen mit dem Hochdurchsatz-Screening und einem effizienten Datenmanagement wird ihre Anwendung den Prozess der Wirkstoffentdeckung zweifelsohne beschleunigen. Urspr¸nglich konzentrierte sich die Kombinatorische Chemie auf die schnelle Synthese von hochkomplexen Gemischen mit winzigen An-

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Solid phase synthesis – designer linkers for combinatorial chemistry: a review

Cited by 15 publications

References 0 publications

Diversity Linker Units for Solid‐Phase Organic Synthesis

Diversity Linker Units for Solid‐Phase Organic Synthesis

Penicillin G Amidase‐Catalysed Hydrolysis of Phenylacetic Hydrazides on a Solid Phase: A New Route to Enzyme‐Cleavable Linkers

Moderne Trennverfahren zur effizienten Aufarbeitung in der organischen Synthese

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