β-Nitro-α-amino acids as latent α,β-dehydro-α-amino acid residues in peptides

Coghlan, Phillip A.; Easton, Christopher J.

doi:10.1016/s0040-4039(99)00839-4

Cited by 19 publications

(8 citation statements)

References 23 publications

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“…At this point, it is clearly evident that a prompt access to α-substituted amides 8 is mandatory for the success of all procedures involving reactive intermediates 9 and 10 . α-Haloamides ( 8 , XCl,Br) have found only occasional utilization as electrophilic substrates because of their instability . α-Oxygenated amides and carbamates ( 8 , XOR 3 , OCOR 3 ) are the most exploited precursors for both N -acylimines 9 and N -acyliminium ions 10 .…”

Section: Introductionmentioning

confidence: 99%

α-Amido Sulfones as Stable Precursors of ReactiveN-Acylimino Derivatives

2005

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Section: Introductionmentioning

confidence: 99%

α-Amido Sulfones as Stable Precursors of ReactiveN-Acylimino Derivatives

2005

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“…86,87 In any event, the intermediate 148 can be isolated by preforming the nitronate salt with a stoichiometric amount of n-BuLi and using N-carbamoylbromoglycinates as Nacylimino equivalents. 88,89 Scheme 38…”

Section: Scheme 37mentioning

confidence: 99%

Recent Advances in Stereoselective Syntheses Using N-Acylimines

Petrini¹,

Torregiani²

2007

Synthesis

112

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The electron-withdrawing aptitude displayed by the acyl group makes N-acylamines very attractive substrates in many processes aimed at the preparation of amino derivatives. The remarkable electrophilicity of N-acylimines can be profitably used to overcome reactivity troubles often observed using N-alkylimines and N-arylimines. The presence of a polar acyl moiety on the nitrogen atom is particularly effective in stereoselective reactions were electrostatic interactions play a major role in determining the facial preference for the nucleophilic attack. Utilization of alkoxycarbonyl groups (e.g. Boc or Cbz) as activating N-acyl substituents allows one to obtain the final amino derivative in a protected form that can be readily cleaved under mild conditions. In this review, several synthetic applications of N-acylimines in stereoselective reactions that have appeared in the literature since 1990 are discussed.

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“…The reaction was stereospecific and proceeds without racemization. used the β-nitro amino acid derivative for the synthesis of α,β-dehydro peptides [7]. Several β-nitro-α-amino acid derivatives were easily prepared and found to be stable to the peptide bond formation.…”

Section: Modification Of Peptides By Formationmentioning

confidence: 99%

Post-assembly Peptide Modifications by Chemical Methods

Kotha¹,

Lahiri

2005

CMC

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The demand for peptide drugs is increasing and in this context, "post-assembly (or post-translational) peptide modification strategies" by chemical manipulation of intact oligo-peptides has provided several analogues. Compounds prepared by this method are useful therapeutic molecules for structure activity studies. Herein, we describe various chemical methods such as cross-coupling reactions, cycloaddition reactions, radical reactions and ring-closing metathesis reactions that are useful for post-translational peptide modifications.

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β-Nitro-α-amino acids as latent α,β-dehydro-α-amino acid residues in peptides

Cited by 19 publications

References 23 publications

α-Amido Sulfones as Stable Precursors of ReactiveN-Acylimino Derivatives

α-Amido Sulfones as Stable Precursors of ReactiveN-Acylimino Derivatives

Recent Advances in Stereoselective Syntheses Using N-Acylimines

Post-assembly Peptide Modifications by Chemical Methods

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