Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 1

Bremner, John B.; Keller, P. A.; Pyne, Stephen G.; Boyle, Timothy P.; Brkić, Zinka; David, Dorothy M.; Robertson, Mark J.; Somphol, Kittiya; Baylis, Dean; Coates, Jonathan; Deadman, John; Jeevarajah, Dharshini; Rhodes, David

doi:10.1016/j.bmc.2010.02.033

Cited by 15 publications

(22 citation statements)

References 25 publications

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“…In much of our work we have been concerned with binaphthyl-based dicationic peptide derivatives, for example the acyclic tripeptides of type 1 (Fig. 1; for example A = CH 2 CH=CH 2 , B = CH 2 Ph, R = CH 2 CH 2 CH(CH 3 ) 2 , MIC against S. aureus 4 μg/mL [6]), which show significant promise as antibacterials [6–8]. In the development of these antibacterials, it became apparent that the nature of the C-terminal amino acid derivative was significant, with indications that the hydrophobic groups at the terminus (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…In the development of these antibacterials, it became apparent that the nature of the C-terminal amino acid derivative was significant, with indications that the hydrophobic groups at the terminus (Fig. 1, group B) [6] and at the α-carbon of the amino acid moiety (Fig. 1, group A) [6–7] were important.…”

Section: Introductionmentioning

confidence: 99%

“…1, group B) [6] and at the α-carbon of the amino acid moiety (Fig. 1, group A) [6–7] were important. In further exploration of the structural space in the latter area, while maintaining benzyl ester functionality at the terminus itself (a free carboxylic acid unit at the C-terminal was deleterious to activity [8]), we envisaged the introduction of two alkyl substituent units incorporated in a ring system at this carbon, resulting in the target compounds 2a – d .…”

Section: Introductionmentioning

confidence: 99%

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Binaphthyl-anchored antibacterial tripeptide derivatives with hydrophobic C-terminal amino acid variations

Bremner¹,

Keller²,

Pyne³

et al. 2012

Beilstein J. Org. Chem.

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SummaryThe facile synthesis of seven new dicationic tripeptide benzyl ester derivatives, with hydrophobic group variations in the C-terminal amino acid component, is described. Moderate to good activity was seen against Gram-positive bacteria in vitro. One cyclohexyl-substituted compound 2c was tested more widely and showed good potency (MIC values ranging from 2–4 μg/mL) against antibiotic-resistant strains of Staphylococcus aureus and Enterococci (VRE, VSE), and against Staphylococcus epidermidis.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Binaphthyl-anchored antibacterial tripeptide derivatives with hydrophobic C-terminal amino acid variations

Bremner¹,

Keller²,

Pyne³

et al. 2012

Beilstein J. Org. Chem.

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“…The title compound was prepared via protocol 1, using 9 [21] (125 mg, 0.236 mmol) and 14 [24] (45 mg, 0.098 mmol) to yield 18 as a white solid (123 mg, 86% …”

Section: Preparation Of Derivativesmentioning

confidence: 99%

“…The title compound was prepared via protocol 1, using 16 (50 mg, 0.11 mmol) and (R)-Lys(BOC)- (21) M A N U S C R I P T …”

Section: Accepted Manuscriptmentioning

confidence: 99%

Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives

Robertson

Bremner

Coates

et al. 2011

European Journal of Medicinal Chemistry

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Design and conformational analysis of peptoids containing N‐hydroxy amides reveals a unique sheet‐like secondary structure

et al. 2011

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N-hydroxy amides can be found in many naturally occurring and synthetic compounds and are known to act as both strong proton donors and chelators of metal cations. We have initiated studies of peptoids, or N-substituted glycines, that contain N-hydroxy amide side chains to investigate the potential effects of these functional groups on peptoid backbone amide rotamer equilibria and local conformations. We reasoned that the propensity of these functional groups to participate in hydrogen bonding could be exploited to enforce intramolecular or intermolecular interactions that yield new peptoid structures. Here, we report the design, synthesis, and detailed conformational analysis of a series of model N-hydroxy peptoids. These peptoids were readily synthesized, and their structures were analyzed in solution by 1D and 2D NMR and in the solidstate by X-ray crystallography. The N-hydroxy amides were found to strongly favor trans conformations with respect to the peptoid backbone in chloroform. More notably, unique sheetlike structures held together via intermolecular hydrogen bonds were observed in the X-ray crystal structures of an N-hydroxy amide peptoid dimer, which to our knowledge represent the first structure of this type reported for peptoids. These results suggest that the N-hydroxy amide can be utilized to control both local backbone geometries and longer-range intermolecular interactions in peptoids, and represents a new functional group in the peptoid design toolbox.

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Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 1

Cited by 15 publications

References 25 publications

Binaphthyl-anchored antibacterial tripeptide derivatives with hydrophobic C-terminal amino acid variations

Binaphthyl-anchored antibacterial tripeptide derivatives with hydrophobic C-terminal amino acid variations

Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives

Design and conformational analysis of peptoids containing N‐hydroxy amides reveals a unique sheet‐like secondary structure

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