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

Rahim, A.; Hidayat, A.; Nurlelasari, N.; Harneti, D.; Supratman, U.; Maharani, R.

Growing Science » Current Chemistry Letters » A total synthesis of cyclodepsipeptide [Leu]6-aureobasidin K using combination of solid- and solution-phase

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Current Chemistry Letters

ISSN 1927-730x (Online) - ISSN 1927-7296 (Print) Quarterly Publication Volume 9 Issue 2 pp. 97-104 , 2020

A total synthesis of cyclodepsipeptide [Leu]6-aureobasidin K using combination of solid- and solution-phase Pages 97-104 Download PDF

Authors: Andi Rahim, Ace Tatang Hidayat, Nurlelasari Nurlelasari, Desi Harneti, Unang Supratman, Rani Maharani

DOI: 10.5267/j.ccl.2019.9.002

Keywords:

Abstract: [Leu]⁶-aureobasidin K 1 is an analog of AbK, in which aIle residue at the sixth position of AbK is replaced by Leu. [Leu]⁶-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 (t_R = 6.49 min) and analysis of structure using ¹H-NMR.

How to cite this paper

 Rahim, A., Hidayat, A., Nurlelasari, N., Harneti, D., Supratman, U & Maharani, R. (2020). A total synthesis of cyclodepsipeptide [Leu]6-aureobasidin K using combination of solid- and solution-phase.Current Chemistry Letters, 9(2), 97-104.

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