Synthesis of cyclols from some small peptides via amide–amide reaction

Lucente, Gino; Romeo, A.

doi:10.1039/c29710001605

Cited by 22 publications

(5 citation statements)

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“…Aminoacyl incorporation reaction was carried out under conditions similar to those described by Stites and Kemp [14] and others [28,29]. The trifluoroacetates 8c,d, 10a,b and 14 were gradually titrated to pH 8.7-9 with NaHCO 3 -Na 2 CO 3 solution in 50% aqueous acetonitrile (2.0-2.5 ml/min).…”

Section: Resultsmentioning

confidence: 99%

Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids

et al. 2005

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A number of protected proline-containing dipeptides Boc-Xaa-Pro-OBu(t) were converted via epimerization-free oxidation with RuO4 to dipeptides with an internal pyroglutamic acid residue, Boc-Xaa-Glp-OBu(t). The latter were subjected to oxidative Hoffman-type rearrangement induced by PhI[OC(O)CF3]2 to give N-(aminoacyl)-pyroglutamates. The behavior of these derivatives under basic conditions was studied, and for two such a derivatives an aminoacyl incorporation reaction was observed, producing otherwise poorly accessible 10-membered-ring dilactams derived from 1,4-diaminobutyric and glutamic acids in practicable yields.

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Section: Resultsmentioning

confidence: 99%

Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids

et al. 2005

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“…The proposal, while intriguing, was eventually discredited by Linus Pauling, who pointed out the implausible thermodynamics of this idea . Nonetheless, examples of substantially smaller cyclol‐containing molecules were eventually uncovered . Despite their thermodynamic instability, cyclols have been implicated in key biological processes such as chromophore maturation in green fluorescent protein (GFP) .…”

Section: Methodsmentioning

confidence: 99%

Cyclols Revisited: Facile Synthesis of Medium‐Sized Cyclic Peptides

Mendoza-Sanchez

Corless

Nguyen

et al. 2017

Chemistry A European J

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Medium-sized rings, particularly the corresponding cyclic peptides, are challenging synthetic targets. In the present study, we report an approach to medium-sized cyclic peptides through targeted formation and collapse of cyclol intermediates. This methodology operates on β-amino imides derived from 2,5-diketopiperazines and offers a straightforward transition from frequently examined scaffolds in drug discovery to a rarely visited class of medium-sized rings.

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“…The C(2)-C(3)-N(4)-C(5) torsion angle of the transamide bond joining the residue of the mercapto acid to the phenylalanine residue is 172.9" whereas the C(5)-C(6)-N(7)-C(ll) torsion angle of the Phe-Pro cis-amide bond is -0.7". The benzylic side group of ( 14) adopts in the crystal a conformation extended toward the phenylalanine nitrogen; this conformation differs from that preferred by (14) in GDC1, solution and from that adopted by the related thiacyclol (1) both in the solid and in s o l ~t i o n . ~…”

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confidence: 85%

“…0.70 mol fraction in CDCl,) is also found in the case of the thiacyclol The 13C n.m.r. spectrum of ( 13) and (14) shows two carbonyl signals and a singlet centred at ca. 6 91, consistent with the presence of a non-protonated carbon atom bonded to three heteroat~ms.~ The mass spectrum shows significant peaks at m/z 332 ( M + ) , 314 (M' -18) and a peak at m/z 245 corresponding to the cyclo-(Phe-Pro) fragment.…”

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confidence: 99%