Literature DB >> 19206132

Integrated oxidative folding of cysteine/selenocysteine containing peptides: improving chemical synthesis of conotoxins.

Aleksandra Walewska1, Min-Min Zhang, Jack J Skalicky, Doju Yoshikami, Baldomero M Olivera, Grzegorz Bulaj.   

Abstract

Building bridges: The use of diselenide and selectively ((15)N/(13)C)-labeled disulfide bridges is combined to give improvements in oxidative folding and disulfide mapping. Conotoxin analogues, each with a pair of selenocysteines (Sec) and labeled cysteines (see scheme, red), exhibited significantly improved folding and the labeled cysteines allow correctly folded species to be rapidly identified by NMR spectroscopy.

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Year:  2009        PMID： 19206132      PMCID： PMC2919336          DOI： 10.1002/anie.200806085

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  23 in total

Review 1.  Synthesis of single- and multiple-stranded cystine-rich peptides.

Authors:  Luis Moroder; Hans-Jürgen Musiol; Marion Götz; Christian Renner
Journal:  Biopolymers       Date:  2005       Impact factor: 2.505

Review 2.  Isosteric replacement of sulfur with other chalcogens in peptides and proteins.

Authors:  Luis Moroder
Journal:  J Pept Sci       Date:  2005-04       Impact factor: 1.905

3.  Novel conotoxins from Conus striatus and Conus kinoshitai selectively block TTX-resistant sodium channels.

Authors:  Grzegorz Bulaj; Peter J West; James E Garrett; Maren Watkins; Maren Marsh; Min-Min Zhang; Raymond S Norton; Brian J Smith; Doju Yoshikami; Baldomero M Olivera
Journal:  Biochemistry       Date:  2005-05-17       Impact factor: 3.162

4.  Oxidative folding of conotoxins sharing an identical disulfide bridging framework.

Authors:  Erika Fuller; Brad R Green; Phil Catlin; Olga Buczek; Jacob S Nielsen; Baldomero M Olivera; Grzegorz Bulaj
Journal:  FEBS J       Date:  2005-04       Impact factor: 5.542

5.  Selenopeptide chemistry.

Authors:  Markus Muttenthaler; Paul F Alewood
Journal:  J Pept Sci       Date:  2008-12       Impact factor: 1.905

6.  The disulfide-coupled folding pathway of apamin as derived from diselenide-quenched analogs and intermediates.

Authors:  S Pegoraro; S Fiori; J Cramer; S Rudolph-Böhner; L Moroder
Journal:  Protein Sci       Date:  1999-08       Impact factor: 6.725

Review 7.  Chalcogen-analogs of amino acids. Their use in X-ray crystallographic and folding studies of peptides and proteins.

Authors:  D Besse; N Budisa; W Karnbrock; C Minks; H J Musiol; S Pegoraro; F Siedler; E Weyher; L Moroder
Journal:  Biol Chem       Date:  1997 Mar-Apr       Impact factor: 3.915

8.  Initial disulfide formation steps in the folding of an omega-conotoxin.

Authors:  Marian Price-Carter; Grzegorz Bulaj; David P Goldenberg
Journal:  Biochemistry       Date:  2002-03-12       Impact factor: 3.162

9.  Synthesis and conformational analysis of apamin analogues with natural and non-natural cystine/selenocystine connectivities.

Authors:  S Fiori; S Pegoraro; S Rudolph-Böhner; J Cramer; L Moroder
Journal:  Biopolymers       Date:  2000-06       Impact factor: 2.505

10.  Isomorphous replacement of cystine with selenocystine in endothelin: oxidative refolding, biological and conformational properties of [Sec3,Sec11,Nle7]-endothelin-1.

Authors:  S Pegoraro; S Fiori; S Rudolph-Böhner; T X Watanabe; L Moroder
Journal:  J Mol Biol       Date:  1998-12-04       Impact factor: 5.469
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  30 in total

1.  μ-conotoxin KIIIA derivatives with divergent affinities versus efficacies in blocking voltage-gated sodium channels.

Authors:  Min-Min Zhang; Tiffany S Han; Baldomero M Olivera; Grzegorz Bulaj; Doju Yoshikami
Journal:  Biochemistry       Date:  2010-06-15       Impact factor: 3.162

2.  Site-specific effects of diselenide bridges on the oxidative folding of a cystine knot peptide, omega-selenoconotoxin GVIA.

Authors:  Konkallu Hanumae Gowd; Viktor Yarotskyy; Keith S Elmslie; Jack J Skalicky; Baldomero M Olivera; Grzegorz Bulaj
Journal:  Biochemistry       Date:  2010-03-30       Impact factor: 3.162

3.  Thiols and selenols as electron-relay catalysts for disulfide-bond reduction.

Authors:  John C Lukesh; Brett Vanveller; Ronald T Raines
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-10       Impact factor: 15.336

4.  Design of a selenylsulfide-bridged EGFR dimerization arm mimic.

Authors:  Laura E Hanold; Christopher P Watkins; Norman T Ton; Peter Liaw; Aaron M Beedle; Eileen J Kennedy
Journal:  Bioorg Med Chem       Date:  2015-03-20       Impact factor: 3.641

5.  Disulfide-Depleted Selenoconopeptides: a Minimalist Strategy to Oxidative Folding of Cysteine-Rich Peptides.

Authors:  Tiffany S Han; Min-Min Zhang; Konkallu Hanumae Gowd; Aleksandra Walewska; Doju Yoshikami; Baldomero M Olivera; Grzegorz Bulaj
Journal:  ACS Med Chem Lett       Date:  2010-05-03       Impact factor: 4.345

6.  A minimized human insulin-receptor-binding motif revealed in a Conus geographus venom insulin.

Authors:  John G Menting; Joanna Gajewiak; Christopher A MacRaild; Danny Hung-Chieh Chou; Maria M Disotuar; Nicholas A Smith; Charleen Miller; Judit Erchegyi; Jean E Rivier; Baldomero M Olivera; Briony E Forbes; Brian J Smith; Raymond S Norton; Helena Safavi-Hemami; Michael C Lawrence
Journal:  Nat Struct Mol Biol       Date:  2016-09-12       Impact factor: 15.369

Review 7.  Structure and function of μ-conotoxins, peptide-based sodium channel blockers with analgesic activity.

Authors:  Brad R Green; Grzegorz Bulaj; Raymond S Norton
Journal:  Future Med Chem       Date:  2014-10       Impact factor: 3.808

8.  Interactions of disulfide-deficient selenocysteine analogs of μ-conotoxin BuIIIB with the α-subunit of the voltage-gated sodium channel subtype 1.3.

Authors:  Brad R Green; Min-Min Zhang; Sandeep Chhabra; Samuel D Robinson; Michael J Wilson; Addison Redding; Baldomero M Olivera; Doju Yoshikami; Grzegorz Bulaj; Raymond S Norton
Journal:  FEBS J       Date:  2014-06-09       Impact factor: 5.542

9.  Expanding chemical diversity of conotoxins: peptoid-peptide chimeras of the sodium channel blocker μ-KIIIA and its selenopeptide analogues.

Authors:  Aleksandra Walewska; Tiffany S Han; Min-Min Zhang; Doju Yoshikami; Grzegorz Bulaj; Krzysztof Rolka
Journal:  Eur J Med Chem       Date:  2013-05-01       Impact factor: 6.514

10.  Manipulating neuronal circuits with endogenous and recombinant cell-surface tethered modulators.

Authors:  Mandë Holford; Sebastian Auer; Martin Laqua; Ines Ibañez-Tallon
Journal:  Front Mol Neurosci       Date:  2009-10-30       Impact factor: 5.639
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