Total Syntheses and Configuration Assignments of JBIR-06 and Related Depsipeptides

Hamada, Chie; Usuki, Yoshinosuke; Takeuchi, Daiki; Ogawa, Hikaru; Abe, Ryota; Satoh, Tetsuya

doi:10.1021/acs.orglett.8b03944

Cited by 2 publications

(2 citation statements)

References 40 publications

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“…During our exploration of antimycin-type antibiotics, 7 we were engaged in studies directed toward the total synthesis and stereochemical assignment of 1 as an approach to perform structure–activity studies on neoantimycins. Herein, we report our success in these endeavours.…”

Section: Introductionmentioning

confidence: 99%

Total synthesis of isoneoantimycin

Usuki¹,

Tanaka²,

Morii³

et al. 2023

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

Total synthesis of isoneoantimycin

Usuki¹,

Tanaka²,

Morii³

et al. 2023

Org. Biomol. Chem.

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“…Depsipeptides are an important class of naturally occurring bioactive compounds, strictly related to peptides, containing at least one ester bond in place of an amide (Stamm et al 2016). Their core structure consists thus of both amide and ester bonds (Hamada et al 2019). The presence of the ester function gives rise to a different conformational behavior compared to peptides, leading to disparate biological activities, from immunosuppressant to antibiotics, from antifungines to anticancers (Sarabia et al 2004).…”

Section: Introductionmentioning

confidence: 99%

On-resin multicomponent 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics

et al. 2019

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Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work, an on resin multicomponent procedure for the synthesis of amidino depsipeptide mimics is described. This approach exploits a metal-free 1,3-dipolar cycloaddition of cyclopentanone -proline enamines and sulfonylazides. In this reaction, the obtained primary cycloadduct undergoes a ring opening and molecular rearrangement giving access to a linear sulfonyl amidine functionalized with both a peptide chain and a diazoalkane. The so obtained diazo function "one pot" reacts with the carboxylic group of N-Fmoc protected amino acids leading to amidino depsipeptide mimics possessing a C4 aliphatic chain.An important advantage of this procedure is the possibility to easily obtain amidino functionalized derivatives that are proteolitically stable peptide bond bioisosters. Moreover, the conformational freedom given by the alkyl chain could promote the obtainment of cyclic depsipeptide with a stabilized secondary structure as demonstrated with both in silico calculations and experimental conformational studies. Finally, labelled depsipeptide mimics can be also synthesized using a fluorescent sulfonylazide in the multicomponent reaction.

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Total Syntheses and Configuration Assignments of JBIR-06 and Related Depsipeptides

Cited by 2 publications

References 40 publications

Total synthesis of isoneoantimycin

Total synthesis of isoneoantimycin

On-resin multicomponent 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics

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