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Molecules
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Disulfide and Diselenide Chemistry
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Disulfide and Diselenide Chemistry

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 December 2012) | Viewed by 18919

Special Issue Editor

Dr. Stevenson Flemer

E-Mail Website
Guest Editor
Department of Chemistry, University of Vermont, Burlington, VT 05405, USA
Interests: peptide synthetic methodology; disulfide and diselenide chemistry

Special Issue Information

Dear Colleagues,

Unique among the elements' chemical properties are the abilities of some of the chalcogens to dimerize covalently, forming linkages which are oxidatively reversible. Disulfide and (to a lesser extent) diselenide bond-forming reactions constitute an important vector of covalent bond construction in organic synthesis, in part due to their well-established reversibility which allows for enhanced molecular engineering potential. Their construction being oxidatively induced primarily through manipulation of reduced thiol and selenol precursors, disulfide and diselenide bond formation expand the repertoire of available strategies for organic chemists toward synthetic design. Although the prevalence of chemical syntheses toward the manufacture of these structural motifs are frequently confined to post-synthetic manipulation of peptide systems, small molecule drug design is increasingly dependent upon the inclusion of disulfide and diselenide-bonded intermediates. Moreover, biological vectors are increasingly recruited in which disulfide and diselenide bridges are artificially inserted or interchanged in native protein structures in order to tune their activity or elucidate the mechanism of action.

This special issue of Molecules encourages the submission of previously unpublished research describing investigative efforts in the area of disulfide and diselenide bond formation, mode-of-action, and physiochemical properties. In addition to synthetic methodology toward the manufacture of disulfide and diselenide architecture, reports pertaining to direct practical application of these structural systems are encouraged.

Dr. Stevenson Flemer 
Guest Editor

Keywords

  • disulfide
  • diselenide
  • selenylsulfide
  • cysteine
  • selenocysteine
  • thiol
  • selenol

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Published Papers (3 papers)

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Research

677 KiB  
Article
Understanding Acid Lability of Cysteine Protecting Groups
by Iván Ramos-Tomillero, Lorena Mendive-Tapia, Miriam Góngora-Benítez, Ernesto Nicolás, Judit Tulla-Puche and Fernando Albericio
Molecules 2013, 18(5), 5155-5162; https://doi.org/10.3390/molecules18055155 - 6 May 2013
Cited by 15 | Viewed by 6809
Abstract
Cys-disulfide bonds contribute to the stabilization of peptide and protein structures. The synthesis of these molecules requires a proper protection of Cys residues, which is crucial to prevent side-reactions and also to achieve the correct Cys connectivity. Here we undertook a mechanistic study [...] Read more.
Cys-disulfide bonds contribute to the stabilization of peptide and protein structures. The synthesis of these molecules requires a proper protection of Cys residues, which is crucial to prevent side-reactions and also to achieve the correct Cys connectivity. Here we undertook a mechanistic study of a set of well-known acid-labile Cys protecting groups, as well other new promising groups, in order to better understand the nature of their acid-lability. The stability of the carbocation generated during the acid treatment was found to have a direct impact on the removal of the protective groups from the corresponding protected Cys-containing peptides. Hence a combination of steric and conjugative effects determines the stability of the carbocations generated. Here we propose diphenylmethyl (Dpm) as a promising protecting group on the basis of its intermediate relative carbocation stability. All the optimized geometries and energies presented in this study were determined using a B3LYP/6-31G(d,p) calculation. The results discussed herein may be of broader applicability for the development of new protecting groups. Full article
(This article belongs to the Special Issue Disulfide and Diselenide Chemistry)
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232 KiB  
Article
Biohybrid -Se-S- Coupling Reactions of an Amino Acid Derived Seleninate
by Mohannad Abdo, Zhexun Sun and Spencer Knapp
Molecules 2013, 18(2), 1963-1972; https://doi.org/10.3390/molecules18021963 - 4 Feb 2013
Cited by 5 | Viewed by 4980
Abstract
We describe the synthesis of the N-(2-seleninatoethyl) amide of N-Boc-phenylalanine, serving here as a peptide model, and its reductive coupling reactions under mild conditions with unprotected thiouridine and glutathione. Selenosulfide products such as these comprise reversibly conjugated bio-components, and can potentially [...] Read more.
We describe the synthesis of the N-(2-seleninatoethyl) amide of N-Boc-phenylalanine, serving here as a peptide model, and its reductive coupling reactions under mild conditions with unprotected thiouridine and glutathione. Selenosulfide products such as these comprise reversibly conjugated bio-components, and can potentially find uses as probes of biological function, such as enzyme inhibitors, delivery systems, or structural mimics. Full article
(This article belongs to the Special Issue Disulfide and Diselenide Chemistry)
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598 KiB  
Article
Investigating Silver Coordination to Mixed Chalcogen Ligands
by Fergus R. Knight, Rebecca A. M. Randall, Lucy Wakefield, Alexandra M. Z. Slawin and J. Derek Woollins
Molecules 2012, 17(11), 13307-13329; https://doi.org/10.3390/molecules171113307 - 8 Nov 2012
Cited by 7 | Viewed by 6282
Abstract
Six silver(I) coordination complexes have been prepared and structurally characterised. Mixed chalcogen-donor acenaphthene ligands L1–L3 [Acenap(EPh)(E'Ph)] (Acenap = acenaphthene-5,6-diyl; E/E' = S, Se, Te) were independently treated with silver(I) salts (AgBF4/AgOTf). In order to keep the number of variables [...] Read more.
Six silver(I) coordination complexes have been prepared and structurally characterised. Mixed chalcogen-donor acenaphthene ligands L1–L3 [Acenap(EPh)(E'Ph)] (Acenap = acenaphthene-5,6-diyl; E/E' = S, Se, Te) were independently treated with silver(I) salts (AgBF4/AgOTf). In order to keep the number of variables to a minimum, all reactions were carried out using a 1:1 ratio of Ag/L and run in dichloromethane. The nature of the donor atoms, the coordinating ability of the respective counter-anion and the type of solvent used in recrystallisation, all affect the structural architecture of the final silver(I) complex, generating monomeric, silver(I) complexes {[AgBF4(L)2] (1 L = L1; 2 L = L2; 3 L = L3), [AgOTf(L)3] (4 L = L1; 5 L = L3), [AgBF4(L)3] (2a L = L1; 3a L = L3)} and a 1D polymeric chain {[AgOTf(L3)]n 6}. The organic acenaphthene ligands L1-L3 adopt a number of ligation modes (bis-monodentate μ2-η2-bridging, quasi-chelating combining monodentate and η6-E(phenyl)-Ag(I) and classical monodentate coordination) with the central silver atom at the centre of a tetrahedral or trigonal planar coordination geometry in each case. The importance of weak interactions in the formation of metal-organic structures is also highlighted by the number of short non-covalent contacts present within each complex. Full article
(This article belongs to the Special Issue Disulfide and Diselenide Chemistry)
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