Acylalkylcarbonates as Acylating Agents for the Synthesis of Peptides

Vaughan, James R.

doi:10.1021/ja01151a554

Cited by 260 publications

(53 citation statements)

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“…Optimised hydrogenation (Pd/C) of 13 cleanly afforded the tribenzylated amino ester 15, which was directly engaged in the peptide coupling reaction without purification. While classical peptidyl coupling conditions (1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole) gave unsatisfactory yields, activation of the Nbenzyloxycarbonyl-protected larginine 16 [23] with isobutyl chloroformate [24] resulted in the formation of the core of miharamycin B 17 in 70 % yield (Scheme 5).…”

Section: Resultsmentioning

confidence: 99%

Stereochemical Assignment and First Synthesis of the Core of Miharamycin Antibiotics

Marcelo

Jiménez‐Barbero

Marrot

et al. 2008

Chemistry A European J

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Section: Resultsmentioning

confidence: 99%

Stereochemical Assignment and First Synthesis of the Core of Miharamycin Antibiotics

Marcelo

Jiménez‐Barbero

Marrot

et al. 2008

Chemistry A European J

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“…In addition, the synthesis of macrocyclic amide and peptido-calixarene derivatives was realized by the use of the potent azide and mixed anhydride coupling methods [21,25], which lead mostly to the formation of optically pure products. The diester derivative 4 was hydrolyzed to the corresponding diacid 5 by 1 N sodium hydroxide.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Macrocyclic Peptido-calix[4]arenes and Peptidopyridines as Precursors for Potential Molecular Metallacages, Chemosensors and Biologically Active Candidates

Amr

Abo-Ghalia

Abdalah³

2006

Zeitschrift Für Naturforschung B

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Novel macrocyclic dipicolinic acid acylated peptides based on upper rim bridged peptidocalix[4]arenes, peptido-pyridines or hybrid structures of both, were synthesized as potential molecular metallacages and chemosensors. While conventional azide or mixed anhydride (ethyl chloroformate) peptide couplings served well for assembling the L-tyrosine or L-ornithine peptide backbones, the acid chloride of pyridine-2,6-dicarboxylic acid (dipicolinic acid) acid served as the complementary acylating agent. The structure assignment of the new compounds was based on chemical and spectroscopic evidences. Some of these compounds exhibit antimicrobial activities.

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“…They could successfully apply the mixed anhydride activation method with isobutyl chloroformate to obtain N-farnesyl dipeptides. Independently we had used this coupling method originally described by Vaughan [21] for our study of the acylation of C[CH 2 NH] pseudodipeptide bonds to yield Fmoc-protected dipeptide units.…”

Section: Acylation Of the Pseudodipeptides With Semiprotected µ-Aminomentioning

confidence: 99%

Synthesis of differentially protectedN-acylated reduced pseudodipeptides as building units for backbone cyclic peptides

et al. 2000

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Backbone cyclization has become an important method for generating or stabilizing the bioactive conformation of peptides without affecting the amino acid side-chains. Up to now, backbone cyclic peptides were mostly synthesized with bridges between N-amino- and N-carboxy-functionalized peptide bonds. To study the influence of a more flexible backbone on the biological activity, we have developed a new type of backbone cyclization which is achieved via the N-functionalized moieties of acylated reduced peptide bonds. As described in our previous publications, the formation of N-functionalized dipeptide units facilitates the peptide assembly compared with the incorporation of N-alkyl amino acids. Besides the racemization-free synthesis of Fmoc-protected pseudodipeptide esters with reduced peptide bonds, the new type of backbone modification allows the use of a great variety of omega-amino- and alpha,omega-dicarboxylic acids differing in chain length and chemical properties. Best results for the coupling of the omega-amino- and alpha,omega-dicarboxylic acids to the reduced peptide bond were obtained by the formation of mixed anhydrides with alkyl chloroformates. Whereas the protecting group combination of Z/OBzl in the dipeptide unit and Boc/OtBu for the N-functionalized moiety leads to the formation of 2-ketopiperazine during hydrogenation, the combination of Fmoc/OtBu and Alloc/OAll is very suitable for the synthesis of backbone cyclic peptides on solid support.

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Acylalkylcarbonates as Acylating Agents for the Synthesis of Peptides

Cited by 260 publications

References 0 publications

Stereochemical Assignment and First Synthesis of the Core of Miharamycin Antibiotics

Stereochemical Assignment and First Synthesis of the Core of Miharamycin Antibiotics

Synthesis of Novel Macrocyclic Peptido-calix[4]arenes and Peptidopyridines as Precursors for Potential Molecular Metallacages, Chemosensors and Biologically Active Candidates

Synthesis of differentially protectedN-acylated reduced pseudodipeptides as building units for backbone cyclic peptides

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