Synthesis and peptide binding properties of a C2 symmetric macrobicycle

Waymark, Christopher P.; Kilburn, Jeremy D.; Gillies, Iain

doi:10.1016/0040-4039(95)00424-b

Cited by 32 publications

(10 citation statements)

References 6 publications

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“…Considerable progress has been made in the recognition of protected peptides. − However, the design and synthesis of artificial receptors capable of interacting with the zwitterionic forms of synthetic or natural peptides remains more challenging. In 1998, Schneider and co-workers set out to create artificial ditopic receptors capable of effecting the selective recognition of zwitterionic peptides in water with length and sequence selectivity .…”

Section: Recognition With Macrocyclic Ion Pair Receptorsmentioning

confidence: 99%

Macrocycles as Ion Pair Receptors

et al. 2019

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Cation and anion recognition have both played central roles in the development of supramolecular chemistry. Much of the associated research has focused on the development of receptors for individual cations or anions, as well as their applications in different areas. Rarely is complexation of the counterions considered. In contrast, ion pair recognition chemistry, emerging from cation and anion coordination chemistry, is a specific research field where co-complexation of both anions and cations, so-called ion pairs, is the center of focus. Systems used for the purpose, known as ion pair receptors, are typically di-or polytopic hosts that contain recognition sites for both cations and anions and which permit the concurrent binding of multiple ions. The field of ion pair recognition has blossomed during the past decades. Several smaller reviews on the topic were published roughly 5 years ago. They provided a summary of synthetic progress and detailed the various limiting ion recognition modes displayed by both acyclic and macrocyclic ion pair receptors known at the time. The present review is designed to provide a comprehensive and up-to-date overview of the chemistry of macrocycle-based ion pair receptors. We specifically focus on the relationship between structure and ion pair recognition, as well as applications of ion pair receptors in sensor development, cation and anion extraction, ion transport, and logic gate construction. CONTENTS 3.4.

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Section: Recognition With Macrocyclic Ion Pair Receptorsmentioning

confidence: 99%

Macrocycles as Ion Pair Receptors

et al. 2019

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“…12). Based on previous reported data [51], macrobicyclic receptor (38) was designed and synthesized, although in moderate overall yield and after many reaction steps [52]. This compound showed to be an effective receptor for dipeptides with a carboxylic acid terminus in CDCl 3 , showing selectivity for N-Cbz--alanyl-L-Xxx-OH dipeptides.…”

Section: Macrocyclic Receptorsmentioning

confidence: 99%

Recent Developments in Chiral Polynitrogenated Synthetic Receptors for Anions

Alfonso

2008

MROC

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In this mini-review, recent chiral receptors bearing polyamine and/or polyamide functional groups are reported. Two main features for their synthesis are the source of the enantiopure nitrogenated synthons and the strategy to assemble the building blocks within the receptor architecture. Combined solutions to both problems have been carried, ranging from chemoenzymatic methods to combinatorial approaches. Topics like conformational control or templation procedures are highlighted. Applications in chiral anion molecular recognition will be also discussed.

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“…In addition, recognition can be encouraged by the large degree of preorganization that is typically found in such molecules. The chiral recognition of amides and carboxylic acids has been demonstrated in macrobicyclic hosts by Still and co-workers and Kilburn and co-workers, respectively. The great potential of polycyclic structures in such studies is well illustrated in a recent publication of Yoon and Still, where a macrotricyclic receptor showed binding of l -amino acid derivatives with enantioselectivites as high as 99% ee.…”

Section: Introductionmentioning

confidence: 96%

Chiral Pyridine-Based Macrobicyclic Clefts: Synthesis and Enantiomeric Recognition of Ammonium Salts

et al. 1996

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An achiral (3) and two chiral pyridine-based macrobicyclic clefts (4 and 5) have been prepared by treating 2,6-bis[[2‘,6‘-bis(bromomethyl)-4‘-methylphenoxy]methyl]pyridine (2) with the appropriate achiral and chiral glycols. Starting 2 was prepared by first treating 2,6-bis(hydroxymethyl)-4-methylphenol with 2,6-[(tosyloxy)methyl]pyridine followed by phosphorus tribromide. Achiral macrobicyclic cleft 3 formed a complex at 25 °C in 50% CH3OH/50% CHCl3 (v/v) with a primary ammonium salt (log K = 3.15) as evidenced by a significant change in the 1H NMR spectrum. Highly organized (S,S,S,S)-4, prepared by treating 2 with (1S,5S)-3-oxapentane-1,5-diol, exhibited recognition at 25 °C in 20% C2H5OH/80% 1,2-C2H4Cl2 (v/v) for the (S)-enantiomer of α-(1-naphthyl)ethylammonium perchlorate (NapEt) over its (R)-form (Δ log K = 0.85). This high recognition factor probably reflects an increase in molecular rigidity by the introduction of a second macro ring on the monocyclic pyridinocrown ligand.

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Synthesis and peptide binding properties of a C2 symmetric macrobicycle

Cited by 32 publications

References 6 publications

Macrocycles as Ion Pair Receptors

Macrocycles as Ion Pair Receptors

Recent Developments in Chiral Polynitrogenated Synthetic Receptors for Anions

Chiral Pyridine-Based Macrobicyclic Clefts: Synthesis and Enantiomeric Recognition of Ammonium Salts

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