Enantioselective binding of dipeptides using acyclic receptors

Botana, Enrique; Ongeri, Sandrine; Arienzo, Rosa; Demarcus, Mariangela; Frey, Jeremy G.; Piarulli, Umberto; Potenza, Donatella; Gennari, Cesare; Kilburn, Jeremy D.

doi:10.1039/b102383g

Cited by 22 publications

(10 citation statements)

References 10 publications

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“…10). 11) [48]. As expected, the selectivity was higher using the more rigid proline derivative (34a) (K ass (D)/K ass (L) = 8.96) than the phenylalanine (34b) counterpart (K ass (D)/K ass (L) = 4.01).…”

Section: Open Chain Receptorssupporting

confidence: 67%

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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Section: Open Chain Receptorssupporting

confidence: 67%

Recent Developments in Chiral Polynitrogenated Synthetic Receptors for Anions

Alfonso

2008

MROC

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“…116 One such macrocyclic structure, 26, has a diamidopyridine unit at the base of an open, bowl-shaped cavity. 118 Macrocycles with up to a 42-membered ring have been reported to form cyclic modular -sheets. NMR spectroscopic studies concluded that macrocycle 26 was a flexible receptor, able to bind Cbz-alanyl-D-alanine substrate within the macrocyclic cavity via a series of well-defined hydrogen bonds making the peptidic substrate an extended conformation.…”

Section: Macrocyclic Peptidomimeticsmentioning

confidence: 99%

Update 1 of: Beta-Strand Mimetics

et al. 2010

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“…(1R*,2R*)-Di-tert-butyl N,N 0 -(cyclohexane-1,2-diyl)dicarbamate, (I), was synthesized as part of our ongoing studies into enantioselective recognition (Botana et al, 2001;Rossi et al, 2002;Kyne et al, 2001). The synthesis of new chiral receptors is a major challenge for chemists since it is very difficult to predict all the factors contributing to the binding process between a host and a guest in solution (Beer et al, 1999).…”

Section: Commentmentioning

confidence: 99%