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

[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. | A total synthesis of cyclodepsipeptide Leu 6-aureobasidin K using combination solid- and solution-phase Current Chemistry Letters 9 2020 97 104 Contents lists available at GrowingScience Current Chemistry Letters homepage A total synthesis of cyclodepsipeptide Leu 6-aureobasidin K using combination of solid- and solution-phase Andi Rahima Ace Tatang Hidayata b Nurlelasaria Desi Harnetia Unang Supratmana b and Rani Maharania b a Department of Chemistry Faculty of Mathematics and Natural Sciences Universitas Padjadjaran Jatinangor West Java Indonesia b Laboratorium Sentral Universitas Padjadjaran Jatinangor West Java Indonesia CHRONICLE ABSTRACT Article history Leu 6-aureobasidin K 1 is an analog of AbK in which aIle residue at the sixth position of Received August 4 2019 AbK is replaced by Leu. Leu 6-AbK 1 was successfully synthesized using a combination of Received in revised form solid- and solution-phase that has a difference with the previous method applied for the August 30 2019 synthesis of other aureobasidin analogues 2S 3S-Hmp -AbL 2. The linear precursor was Accepted September 27 2019 prepared by using solid-phase method with Fmoc strategy in which an ester bond was Available online constructed on the resin. The cyclic product was obtained from a solution-phase reaction of September 28 2019 the linear precursor using HATU reagent. The crude of the cyclic peptide was purified using Keywords a column chromatography technique to obtain Leu 6-AbK 1 with a percent yield of Aureobasidin DIC DMAP that is higher compared to previous similar method for synthesis of 2S 3S-Hmp -AbL 2. The Leu 6-Aureobasidin K 1 purity level of cyclic product was analyzed using analytical RP-HPLC tR min and N-methylated analysis of structure using 1H-NMR. cyclononadepsipeptide Solid-phase peptide synthesis 2020 Growing Science Ltd. All rights reserved. 1. Introduction Aureobasidins are a class of cyclodepsipeptides isolated from black yeast .