Vinylogous polypeptides: an alternative peptide backbone

Hagihara, Masahiko; Anthony, Neville J.; Stout, Thomas J.; Clardy, Jon; Schreiber, Stuart L.

doi:10.1021/ja00042a052

Cited by 273 publications

(172 citation statements)

References 3 publications

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“…[1] Heterogeneous backbones, composed of two or more residue types, can also display well-defined folding behavior, although this strategy for foldamer design has received relatively little attention to date. [3] The exploration of heterogeneous backbones is important because mixing monomer classes leads to an exponential increase in the range of potential foldamers. Increasing the number of distinct shapes that can be predictably achieved should enhance opportunities to endow foldamers with desirable activities.…”

mentioning

confidence: 99%

Two Helical Conformations from a Single Foldamer Backbone: “Split Personality” in Short α/β‐Peptides

Hayen¹,

Schmitt²,

Ngassa³

et al. 2004

Angew Chem Int Ed

211

127

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Oligomers that adopt predictable conformations ("foldamers") are subjects of increasing interest from the perspectives of both fundamental research and applications.[1] The study of unnatural oligomers that display secondary structures analogous to those of proteins or nucleic acids provides new insight on the parameters that influence the "foldability" of a backbone, e.g., the relationships between conformational stability and number of residues or residue flexibility. As the rules that govern shape are elucidated for new backbones, this

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mentioning

confidence: 99%

Two Helical Conformations from a Single Foldamer Backbone: “Split Personality” in Short α/β‐Peptides

Hayen¹,

Schmitt²,

Ngassa³

et al. 2004

Angew Chem Int Ed

211

127

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“…Many of these are structural variants of polypeptides, such as polycarbamates (3), peptide nucleic acids (4), and vinylogous polypeptides (5). Recent efforts have yielded oligomers with defined folding propensities such as oligoanthranilamides (6), vinylogous sulfonamidopeptides (7), ''aedemers'' (8), and oligophenylacetylenes (31).…”

mentioning

confidence: 99%

Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure

Kirshenbaum

Barron

Goldsmith

et al. 1998

Proc. Natl. Acad. Sci. U.S.A.

455

390

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We have synthesized and characterized a family of structured oligo-N-substituted-glycines (peptoids) up to 36 residues in length by using an efficient solid-phase protocol to incorporate chemically diverse side chains in a sequence-specific fashion. We investigated polypeptoids containing side chains with a chiral center adjacent to the main chain nitrogen. Some of these sequences have stable secondary structure, despite the achirality of the polymer backbone and its lack of hydrogen bond donors. In both aqueous and organic solvents, peptoid oligomers as short as five residues give rise to CD spectra that strongly resemble those of peptide ␣-helices. Differential scanning calorimetry and CD measurements show that polypeptoid secondary structure is highly stable and that unfolding is reversible and cooperative. Thermodynamic parameters obtained for unfolding are similar to those obtained for the ␣-helix to coil transitions of peptides. This class of biomimetic polymers may enable the design of self-assembling macromolecules with novel structures and functions.

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“…It should be noted that the synthesis of allyl bromide 4 was always accompanied by the formation of its regioisomer 5, which was easily separable from the desired product 4 by silica gel column chromatography (Scheme 3). In order to establish a chemical library reserved for the various functionalized allylamines published during the last decade by our research group 30 and their use as basic skeletons of many biologically important substances [31][32][33][34][35][36][37] and numerous natural products [38][39][40][41][42][43][44][45][46][47] , we focused our attention on the synthesis of a new family of allylamines 6. The best reaction conditions were obtained following the reaction of the electrophilic allyl bromide (E)-4 with excess of monoalkylamines (2 equiv.)…”

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confidence: 99%

Efficient synthesis of allylamines from a novel (E)-2,3-difunctionalized allyl bromide

Ameur¹,

Arfaoui²

2014

Arkivoc

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We report a new procedure for highly stereoselective synthesis of difunctionalized allyl and vinyl bromides E-4 and E-5 via a tandem reaction of bromination-dehydrobromination of tetraethyl prop-2-ene-1,2-diyldiphosphonate in the presence of DBU in acetonitrile at room temperature. The coupling reaction of allyl bromide E-4 with various primary amines in methanol at 0 °C, followed by S N 2' reaction, provides a new family of tetraethyl 1-(alkylamino)prop-2-ene-1,2-diyldiphosphonates 6 in high yields.

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Vinylogous polypeptides: an alternative peptide backbone

Cited by 273 publications

References 3 publications

Two Helical Conformations from a Single Foldamer Backbone: “Split Personality” in Short α/β‐Peptides

Two Helical Conformations from a Single Foldamer Backbone: “Split Personality” in Short α/β‐Peptides

Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure

Efficient synthesis of allylamines from a novel (E)-2,3-difunctionalized allyl bromide

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