Solid-Phase Synthesis of Oxathiocoraline by a Key Intermolecular Disulfide Dimer

Tulla‐Puche, Judit; Bayó‐Puxán, Núria; Moreno, Juan Antonio; Francesch, Andrés; Cuevas, Carmen; Álvarez, Mercedes; Alberício, Fernando

doi:10.1021/ja0686312

Cited by 43 publications

(52 citation statements)

References 8 publications

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“…Finally, and although less frequent, internal diketopiperazine formation involving the NH and the activated carboxylic acid of the previous amino acid has been reported ( Figure 2). 7 Protection of this amide bond can result in the suppression or at least minimization of these undesired interactions. Thus, it has been described that solid-phase synthesis (SPS) of long peptides with sequences prone to aggregation can be improved by protecting some of the amides of the peptide.…”

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confidence: 99%

EDOTn and MIM, new peptide backbone protecting groups

et al. 2008

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In recent years, backbone protection has allowed the synthesis of complex peptidic sequences of high interest by preventing chain aggregation and aspartimides formation. Nevertheless, the backbone protectors currently used have some drawbacks: they are difficult to remove and show high steric hindrance. The new backbone protectors presented in this study (EDOTn and MIM) represent an improvement in both aspects. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 90: 444–449, 2008.This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley. com

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EDOTn and MIM, new peptide backbone protecting groups

et al. 2008

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“…[1] Differing only in one of the NMe residues, triostin A bears an NMe-Val, whereas triostin B and C contain an NMe-Ile and an N,g-dimethyl-allo-Ile, respectively. [2] Triostin A, as well as other members of this family, which include echinomycin, [3] BE-22179, [4] and thiocoraline [5,6] show antibacterial and cytotoxic activity. [7] Triostin A binds to DNA by bisintercalation [8] through its two quinoxaline units and shows CpG selectivity.…”

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confidence: 99%

Protection by Conformationally Restricted Mobility: First Solid‐Phase Synthesis of Triostin A

Tulla‐Puche¹,

Marcucci²,

Fermin³

et al. 2008

Chemistry A European J

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Conformationally restricted mobility: The application of an efficient solid‐phase strategy based on protection by conformationally restricted mobility (see scheme) has allowed, for the first time, the synthesis and determination of the biological activity of the two triostin A conformers, which result from the isomerization cis/trans of the N‐methyl group of Cys. The most polar conformer showed the greatest inhibitory effect on cell growth.

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“…In www.eurjoc.orgthese first attempts, either 3-hydroxyquinaldic acid (3-HQA) or commercial quinaldic acid (QNA) were used (Scheme 11). 4 ] was clean, without cleavage of the ester functionality. pNZ-Cys(Acm)-OH was coupled as a fourth amino acid, providing the tetradepsipeptide in good purity (Entry 3).…”

Section: B) Ester Stability Within the Peptide Chainmentioning

confidence: 99%

“…Oxathiocoraline [4] is a bicyclic depsipeptide with C 2 symmetry. It is made up of two antiparallel tetrapeptide chains linked by two ester bonds and an additional disulfide bridge in the central part of the molecule (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Recently, the first synthesis of oxathiocoraline has been achieved by an optimized solid-phase approach, through a key intermolecular disulfide bond formation on solid-support. [4] Together with its amide analogue, [5,6] oxathiocoraline was designed with the aim of producing a more resistant compound displaying antitumour activity comparable to that of the natural compound thiocoraline. [7,8] Here we discuss and analyse the procedures followed to achieve the synthesis of oxathiocoraline.…”

Section: Introductionmentioning

confidence: 99%

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Oxathiocoraline: Lessons to be Learned from the Synthesis of ComplexN‐Methylated Depsipeptides

2009

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Investigations into the synthesis of oxathiocoraline, a bicyclic depsipeptide with C2 symmetry, revealed a number of unexpected side‐reactions that could not be circumvented by classical or standard means. This cyclodepsipeptide has a large number of N‐methyl amino acids coexisting with two ester bonds and also shows a branched structure; these features hinder its synthesis. In addition, complexity is further increased because of the presence of a large number of non‐commercially available cysteines and heterocyclic moieties. Here we describe the general points that should be addressed when attempting the synthesis of a cyclodepsipeptide, such as strategies to prevent or minimize diketopiperazine formation, β‐elimination, and oxidation byproducts. The optimum design includes a suitable solid support, the choice of the best starting point for the synthesis (first amino acid to anchor to the resin) and a set of compatible and/or protecting groups and coupling reagents.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Solid-Phase Synthesis of Oxathiocoraline by a Key Intermolecular Disulfide Dimer

Cited by 43 publications

References 8 publications

EDOTn and MIM, new peptide backbone protecting groups

EDOTn and MIM, new peptide backbone protecting groups

Protection by Conformationally Restricted Mobility: First Solid‐Phase Synthesis of Triostin A

Oxathiocoraline: Lessons to be Learned from the Synthesis of ComplexN‐Methylated Depsipeptides

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