Literature DB >> 15653327

N-acyl-N-alkyl-sulfonamide anchors derived from Kenner's safety-catch linker: powerful tools in bioorganic and medicinal chemistry.

Philipp Heidler1, Andreas Link.   

Abstract

In 1971 Kenner et al. introduced the safety-catch principle into solid phase peptide synthesis. Thus two contradicting needs were addressed. On the one hand, sufficient stability of the linker substrate bond to impede hydrolysis or similar side reactions, on the other hand mild chemical conditions allowing for unscathed liberation of the precious products. Over the years this linker type emerged in several different chemical disciplines and nowadays it presents a useful and broadly applicable tool. Recent advancements and applications based on Kenner's safety-catch linker are reviewed.

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Year:  2005        PMID: 15653327     DOI: 10.1016/j.bmc.2004.10.045

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  6 in total

1.  A convenient approach to synthesizing peptide C-terminal N-alkyl amides.

Authors:  Wei-Jie Fang; Tatyana Yakovleva; Jane V Aldrich
Journal:  Biopolymers       Date:  2011-02-09       Impact factor: 2.505

2.  Inhibitors of adenosine consuming parasites through polymer-assisted N-acylation of N6-substituted 5'-amino-5'-deoxyadenosines.

Authors:  Vida Zohrabi-Kalantari; Philipp Heidler; Marcel Kaiser; Reto Brun; Christoph Kamper; Andreas Link
Journal:  Mol Divers       Date:  2009-06-26       Impact factor: 2.943

3.  N-[(4-Methyl-phen-yl)sulfon-yl]acetamide.

Authors:  Hoong-Kun Fun; Tze Shyang Chia; Poornima Hegde; K Jyothi; Pramila Rita D'Souza
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-13

Review 4.  Advances in Fmoc solid-phase peptide synthesis.

Authors:  Raymond Behrendt; Peter White; John Offer
Journal:  J Pept Sci       Date:  2016-01       Impact factor: 1.905

5.  Facile Synthesis of a Next Generation Safety-Catch Acid-Labile Linker, SCAL-2, Suitable for Solid-Phase Synthesis, On-Support Display and for Post-Synthesis Tagging.

Authors:  Christophe Portal; Martin Hintersteiner; Olivier Barbeau; Peter Dodd; Margaret Huggett; Irene Pérez-Pi; David Evans; Manfred Auer
Journal:  ChemistrySelect       Date:  2017-08-16       Impact factor: 2.109

6.  Rapid labelling and covalent inhibition of intracellular native proteins using ligand-directed N-acyl-N-alkyl sulfonamide.

Authors:  Tomonori Tamura; Tsuyoshi Ueda; Taiki Goto; Taku Tsukidate; Yonatan Shapira; Yuki Nishikawa; Alma Fujisawa; Itaru Hamachi
Journal:  Nat Commun       Date:  2018-05-14       Impact factor: 14.919

  6 in total

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