A total synthesis of a highly N-methylated cyclodepsipeptide [2S,3S-Hmp]-aureobasidin L using solid-phase methods

Maharani, Rani; Brownlee, Robert T. C.; Hughes, Andrew B.; Abbott, Belinda M.

doi:10.1016/j.tet.2014.02.036

Cited by 24 publications

(34 citation statements)

References 40 publications

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“…It seems likely that diketopiperazine (DKP) formation might take place during the Fmoc deprotection using piperidine. A similar finding has been reported by Maharani et al 7 in the total synthesis of [2S,3S-Hmp] AbL 2. Therefore, a protocol employing 10% DBU in DMF was applied for the deprotection of Fmoc-group by 2x10 seconds to suppress the DKP formation.…”

Section: Resultssupporting

confidence: 89%

“…methylated amino acids and one hydroxy acid. The structure 3 To date, there are only four papers describing total synthesis of aureobasidin, where three of the synthesis were carried out in solution phase [4][5][6] and one synthesis was undertaken using a combination of solid-and solution-phase method 7 . The later method, applied for the synthesis [2S,3S-Hmp]aureobasidin L 2 (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…1), was found to be faster than the previous three methods, although the yield of synthesis was still low. In the synthesis of [2S,3S-Hmp]-aureobasidin L 2, Maharani et al 7 synthesized an ester bond of [2S,3S-Hmp]-AbL 2 in solution-phase as a depsidipeptide substructure of Fmoc-MeVal-O-Hmp-OH 3. This depsidipeptide was then attached onto the peptidyl resin to construct the linear peptide with an overall yield of 1.89%.…”

Section: Introductionmentioning

confidence: 99%

“…In this current report, [Leu] 6 -aureobasidin K 1 was chosen as target of synthesis. The strategy of the synthesis was similar to the strategy used by Maharani et al 7 which is through a combination of solidand solution-phase methods. However, a different approach of the synthesis was applied.…”

Section: Introductionmentioning

confidence: 99%

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A total synthesis of cyclodepsipeptide [Leu]6-aureobasidin K using combination of solid- and solution-phase

Rahim¹

2020

10.5267/j.ccl

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AbK 1 was successfully synthesized using a combination of solid-and solution-phase that has a difference with the previous method applied for the synthesis of other aureobasidin analogues, [2S,3S-Hmp]-AbL 2. The linear precursor was prepared by using solid-phase method with Fmoc strategy, in which an ester bond was constructed on the resin. The cyclic product was obtained from a solution-phase reaction of the linear precursor using HATU reagent. The crude of the cyclic peptide was purified using a column chromatography technique to obtain [Leu] 6-AbK 1 with a percent yield of 5.31% that is higher compared to previous similar method for synthesis of [2S,3S-Hmp]-AbL 2. The purity level of cyclic product was analyzed using analytical RP-HPLC (tR = 6.49 min) and analysis of structure using 1 H-NMR.

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Section: Resultssupporting

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A total synthesis of cyclodepsipeptide [Leu]6-aureobasidin K using combination of solid- and solution-phase

Rahim¹

2020

10.5267/j.ccl

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“…Senyawa ini menjadi metabolit sekunder dari sejumlah tumbuhan dan fungi atau makhluk hidup dari lingkungan perairan laut (Seger et al, 2004;Sabareesh et al, 2007;Krska et al, 2008). Senyawa-senyawa siklodepsipeptida telah banyak dilaporkan memiliki aktivitas biologis seperti aktivitas antimikroba, anti tumor ataupun sebagai pestisida (Wang & Xu 2012;Maharani et al, 2014;Suzuki et al, 1977). Anggota dari kelompok senyawa siklodepsipeptida sangat berpotensi sebagai obat medik baru di dunia kedokteran.Aktivitas biologi yang sangat menarik ditunjukkan oleh senyawasenyawa kelompok siklodepsipeptida seperti efek immunesuppresan, antibiotik, antijamur, serta antikanker (Lemmens-Gruber et al, 2009).…”

Section: Pendahuluanunclassified

Sintesis Prekursor Senyawa Beauvericin, Asam (2r)-Asetiloksiisovalerat

2015

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Abstrak: Beauvericin merupakan heksadepsipeptida siklik yang diproduksi oleh berbagai jamur seperti Beauveria bassiana dan Fussarium spp. Penelitian mengenai sintesis senyawa beauvericin telah dilakukan melalui media mikrobiologi, namun sintesis dengan metode sintesis peptida masih belum banyak dilaporkan. Sedikitnya laporan mengenai sintesis senyawa beauvericin disebabkan sulitnya akses terhadap pengadaan material sintesis atau prekursor senyawa yang bersangkutan.Prekursor dari senyawa beauvericin adalah asam amino N-metilfenilalanin dan asam hidroksi isovalerat. Dalam kaitannya dengan sintesis total peptida dalam fase padat yang akan dilakukan, asam hidroksi isovalerat (Hiv) akan sulit ditambahkan ke dalam resin, sehingga senyawa ini harus ditambahkan kedalam resin dalam bentuk depsidipeptida, Fmoc-MePhe-Hiv.Sintesis depsidipeptida ini merupakan rangkaian 4 tahap reaksi, yakni, diazotisasi-perlindungan t-Bu-pelepasan asetiloksi-kopling.Dalam penelitian ini,tahap diazotisasi akan dilaporkan. Asam (2R)-asetiloksiisovalerat disintesis dari D-valin melalui reaksi pembentukan garam diazonium dengan penambahan NaNO 2 dan asam asetat.Proses sintesis dikontrol dengan kromatografi lapis dan dimurnikan dengan metode kromatografi kolom terbuka. Produk sintesis dikarakterisasi dengan berbagai teknik spektroskopi meliputi spektrofotometer inframerah, spektroskopi massa (LC-MS), 1 H-NMR dan 13 C-NMR. Senyawa asam (2R)-asetiloksiisovalerat diperoleh dengan rendemen 62,7%. Kata kunci:Beauvericin, asam (2R)-asetiloksiisovalerat, NaNO 2 , and asam asetat glasial. Abstract: Beauvericin is a cyclic hexapeptide produced by various fungi such as Beauveria bassiana and Fussarium spp. Research on the synthesis of beauvericin has been carried out through microbiological media, but the synthesis using a chemical synthesis method has not been widely reported. The limited articles about the synthesis of beauvericin is due to the difficulty of access to the procurement of materials synthesis or precursor compound. Beauvericin contains of precursors of N-metilfenilalanin amino acids and D-hydroxyisovaleric acid.Since the synthesis of beauvericin will be undertaken using a solid phase method, it will be difficult to add Dhydroxyisovaleric

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ChemInform Abstract: A Total Synthesis of a Highly N‐Methylated Cyclodepsipeptide [2S,3S‐Hmp]‐Aureobasidin L Using Solid‐Phase Methods.

et al. 2014

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A total synthesis of a highly N-methylated cyclodepsipeptide [2S,3S-Hmp]-aureobasidin L using solid-phase methods

Cited by 24 publications

References 40 publications

A total synthesis of cyclodepsipeptide [Leu]6-aureobasidin K using combination of solid- and solution-phase

A total synthesis of cyclodepsipeptide [Leu]6-aureobasidin K using combination of solid- and solution-phase

Sintesis Prekursor Senyawa Beauvericin, Asam (2r)-Asetiloksiisovalerat

ChemInform Abstract: A Total Synthesis of a Highly N‐Methylated Cyclodepsipeptide [2S,3S‐Hmp]‐Aureobasidin L Using Solid‐Phase Methods.

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