Linker For Solid-phase Synthesis Research Articles

A new germanium based linker for solid phase synthesis of aromatic compounds

An efficient three-step synthesis of germyl linker precursor 4 is described which enables a simple two step immobilisation of lithiated aromatics to Argogel™ polymer; cleavage from the polymer support via ipso-degermylation with TFA, ICl, Br2 and NCS provides protio-, iodo-, bromo- and chloro- aryls, respectively.

A novel, thioacetal based linker for solid-phase synthesis

Commercially available (±)-α-lipoic acid was employed as a novel, chemically robust linker for the immobilization of ketones. The utility of this thioacetal based linker in solid-phase synthesis was demonstrated by synthesizing several 4-acetylbiphenyls and 4-alkoxyacetophenones via Suzuki and Mitsunobu reactions, respectively. The products were easily cleaved from solid support by treatment with [bis(trifluoroacetoxy)iodo]benzene.

Design and synthesis of silyl ether-based linker for solid-phase synthesis of glycopeptides

A novel silyl linker was designed to facilitate the solid-phase synthesis of protected glycopeptide blocks. Alcohols (carbohydrate, serine, or threonine) were silylated with trialkylchlorosilane containing the p-nitrophenyl group. The nitro group was reduced and succinylated to give the succinanilic acids, which were attached to the glycine-preloaded resin via activation with HBTU/HOBt. After elongation of the peptide chain by segment condensation or Fmoc chemistry-based stepwise method, the synthesized glycopeptides in the protected form were split from the resin by fluoridolysis.

A Surprising Solid-Phase Effect: Development of a Recyclable "Traceless" Linker System for Reactions on Solid Support.

Triazenes as "traceless" linkers for solid-phase synthesis have been utilized for the attachment of arenes to a solid support and yield the corresponding products after various organometallic reactions (Heck reaction and asymmetric dihydroxylation, see the reaction scheme) and cycloadditions (Diels-Alder reaction). The triazene linker is distinguished by its accessibility, thermal robustness, and capability to undergo regeneration.

9-Hydroxy-9-(4-carboxyphenyl)fluorene — a new linker for solid phase synthesis

The convenient synthesis of 9-hydroxy-9-(4-carboxyphenyl)fluorene and its application as a new linker for solid phase synthesis is reported. The loading of the resin-bound linker with carboxylic acids as well as the cleavage conditions were investigated. The release of the carboxylic acids from this system by treatment with acids is hampered due to the electron-withdrawing effect of the carboxamide group in the para position of the phenyl ring of the resin-bound linker.

Traceless Linkers for Solid-phase Synthesis. Homo- and Hetero-Diels-Alder Reactions of o-Quinodimethanes

Traceless Linkers for Solid-phase Synthesis. Homo- and Hetero-Diels-Alder Reactions of <i>o</i>-Quinodimethanes

Aryl hydrazides as linkers for solid phase synthesis which are cleavable under mild oxidative conditions

We have developed and acid/base stable aryl hydrazide linker which is readily coupled to solid phase resins. Cleavage is specific and facile, requiring a copper (II) catalyst, base and a nucleophile to proceed. The conditions are compatible with all 20 proteinogenic amino acids and quantitative cleavage is achieved within 2 hours at 20°C to give peptides with C-terminal acid, amide or ester functionalities. Aryl hydrazides also offer scope as simple “traceless” linkers.

Versatile Dde-based primary amine linkers for solid phase synthesis

Linkers based on the Dde primary amine protecting strategy have been developed and their utility demonstrated in the solid phase synthesis of a naturally occurring spider toxin. The linkers are stable to both acid and base conditions and cleaved either with 2% v/v hydrazine hydrate or by transamination with a volatile primary alkylamine in a variety of organic solvents.

A highly acid labile silicon linker for solid phase synthesis

Abstract A novel arylsilane based linker has been prepared for the solid phase synthesis of small molecule combinatorial libraries. Efficient cleavage is achieved using TFA via anchimerically assisted protiodesilylation to yield aromatic products possessing no residual linker functionality.

Six new photolabile linkers for solid phase synthesis. 2. Coupling of various building blocks and photolytic cleavage.

Photolabile linkers are very useful in the generation of combinatorial libraries as they offer compound cleavage under mild conditions directly into a solvent suitable for biological testing. Six new photolabile linkers have been developed which allow coupling of building blocks with a carboxy, amino, hydroxy and sulfonyl group. Photolytic cleavage of these building blocks will give libraries with carboxy, amido, methylamido, amino, ureido, hydroxy, aminocarbonyloxy and aminosulfonyl terminal groups. Coupling conditions for these reactions were elucidated and the photolytic cleavage reaction was studied.

A new o-nitrobenzyl photocleavable linker for solid phase synthesis

A new photolabile linker, 7, was synthesized in high yield from commercially available starting materials. Irradiation of polymer supports containing 7 produced the desired amino acid and sugar products in high yields. The utility of 7 was demonstrated through the synthesis and photocleavage of a branched trimannan from a polymer support.

New fluoride-labile linkers for solid-phase organic synthesis

Silyl-linkers 2 and 3 are shown to be useful linkers for solid-phase synthesis. They can be cleaved by fluoridolysis under basic (TBAF) or neutral (CsF) conditions. Methods for the synthesis, loading and release are described.

The use of a dithiane protected benzoin photolabile safety catch linker for solid-phase synthesis

The dithiane protected benzoin group is shown to be a useful safety catch photolabile linker in solid-phase synthesis. Methods for the synthesis, loading, deprotection and photolysis of the linker are described.

Six new photolabile linkers for solid-phase synthesis. 1. Methods of preparation.

In the synthesis of combinatorial chemical libraries on solid phase, there is a need to cleave the compounds from the solid support before the library can be tested for biological activity. It is advantageous to use linkers which will release the libraries by mild photolytic cleavage. We have developed six new linkers of the photosensitive alpha-methyl 2-nitrobenzyl type containing amino, hydroxy, bromo and methylamino groups, and also 4-nitrophenoxycarbonyl activated OH and NH2 groups.

Activation Method to Prepare a Highly Reactive Acylsulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis1

Activation Method to Prepare a Highly Reactive Acylsulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis¹

Reagents for Combinatorial Organic Synthesis: Development of a New o-Nitrobenzyl Photolabile Linker for Solid Phase Synthesis

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReagents for Combinatorial Organic Synthesis: Development of a New o-Nitrobenzyl Photolabile Linker for Solid Phase SynthesisChristopher P. Holmes and David G. JonesCite this: J. Org. Chem. 1995, 60, 8, 2318–2319Publication Date (Print):April 1, 1995Publication History Published online1 May 2002Published inissue 1 April 1995https://doi.org/10.1021/jo00113a004RIGHTS & PERMISSIONSArticle Views2186Altmetric-Citations185LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (1 MB) Get e-AlertsSupporting Info (2)»Supporting Information Supporting Information Get e-Alerts