Part II Publications in peer-reviewed journals
- Xiao, Y.; Jiang, Y.; Xu, C.; Nakliang, P.; Yoon, S.; Choi, S.; Guo, Y.; Ye, T., Total synthesis of thioamycolamide A using diastereoselective sulfa-Michael addition as the key step. Organic Chemistry Frontiers 2022, 9 (15), 3998-4002.
Abstract: The stereocontrolled total synthesis of the antitumor natural product thioamycolamide A has been accomplished in 14 longest linear steps and an overall yield of 19.1%. The central feature of our convergent route to this family of novel macrocyclic natural products is the preparation of the β-alkylthio amide subunit through an auxiliary-controlled, diastereoselective sulfa-Michael addition.
- Wu, F., Zhang, T., Yu, J., Guo, Y., Ye, T. Total Synthesis and Structural Reassignment of Laingolide A. Mar. Drugs 2021, 19, 247-265. Abstract: The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide.
- Wu, F., Yu, J., Meng, J., Guo, Y., Ye, T. Total Synthesis of Pagoamide A. Molecules 2021, 26, 4224-4240. Abstract: The first total synthesis of the thiazole-containing cyclic depsipeptide pagoamide A, is detailed. The longest linear sequence of the liquid-phase synthesis comprises 9 long linear steps from simple known starting materials, which led to the unambiguous structural confirmation of pagoamide A.
- “Biochemistry-Guided Prediction of the Absolute Configuration of Fungal Reduced Polyketides” Takino, Junya, Akari Kotani, Taro Ozaki, Wenquan Peng, Jie Yu, Yian Guo, Susumu Mochizuki, Kazuya Akimitsu, Masaru Hashimoto, Tao Ye, Atsushi Minami, and Hideaki Oikawa Angewandte Chemie International Edition 2021, 60: 23403-11.
Abstract: Highly reducing polyketide synthases (HR-PKSs) produce structurally diverse polyketides (PKs). The PK diversity is constructed by a variety of factors, including the beta-keto processing, chain length, methylation pattern, and relative and absolute configurations of the substituents. We examined the stereochemical course of the PK processing for the synthesis of polyhydroxy PKs such as phialotides, phomenoic acid, and ACR-toxin. Heterologous expression of a HR-PKS gene, a trans-acting enoylreductase gene, and a truncated non-ribosomal peptide synthetase gene resulted in the formation of a linear PK with multiple stereogenic centers. The absolute configurations of the stereogenic centers were determined by chemical degradation followed by comparison of the degradation products with synthetic standards. A stereochemical rule was proposed to explain the absolute configurations of other reduced PKs and highlights an error in the absolute configurations of a reported structure. The present work demonstrates that focused functional analysis of functionally related HR-PKSs leads to a better understanding of the stereochemical course.
Abstract: The first total synthesis of antiallergic depsipeptide seongsanamide A has been achieved and also confirmed the relative and absolute stereochemistry of the natural product. Highlights of the convergent route include the use of Miyuara borylation, Chan-Evans-Lam coupling for the effective assembly of isodityrosine subunit and the identification of an effective macrocyclization site in very high conversion. The longest linear sequence leading to seongsanamide A was 12 steps, with an overall yield of 12.7%.
6. “Nine-Step Total Synthesis and Biological Evaluation of Rhizonin A” Qingchao Liu, Langlang Liu, Ranjala Ratnayake, Hendrik Luesch, Yian Guo, Tao Ye Chinese Journal of Chemistry 2020, 38, 1280-4
Abstract: We have achieved the total synthesis of an architecturally and biologically intriguing cyclic polypeptide, rhizonin A (1), in an exceptionally concise and convergent fashion. The strategic route entails 9 longest linear steps to elaborate commercially available materials into the natural product with an overall yield of 9.7%. The brevity of sequence and high overall yield was fueled by the judicious selection of chemical tactics. Rhizonin A (1) showed weak inhibitory effects on the cell viability of HCT116 colorectal cancer cells and this activity was dependent on hypoxia-inducible factors.
7. “Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl2-Catalyzed Intramolecular [3+2] Cycloaddition” Xuelei Jia, Honghui Lei, Feipeng Han, Tao Zhang, Ying Chen, Zhengshuang Xu, Pratanphorn Nakliang, Sun Choi, Yian Guo, Tao Ye Chem. Int. Ed. 2020, 59, 12832-6
Abstract: A concise and asymmetric total synthesis of five kopsane alkaloids which share a unique heptacyclic caged ring system was accomplished. The key transformation in our sequence involved a remarkable PtCl2 catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3-quaternary functionalized indoline. Expeditious construction of diverse indoline scaffolds with excellent control of diastereoselectivity demonstrated the broad scope and versatility of this key transformation
8. “Total Synthesis and Biological Evaluation of Kakeromamide A and Its Analogues” Meng Zhao, Yi Xiao, Satoshi Otsuka, Yoichi Nakao, Yian Guo1, Tao Ye Frontiers in Chemistry 2020, 8, doi: 10.3389/fchem.2020.00410
Abstract: Kakeromamide A (1), the first marine cyclopeptide inducing neural stem cells differentiation into astrocytes, was synthesized in 12 longest linear steps and 14% overall yield. Using this synthetic approach, four analogues of kakeromamide A were prepared and evaluated for neural differentiation- modulating activity.
9. “Proteomic study reveals the involvement of energy metabolism in the fast antidepressant effect of (2R, 6R)-hydroxy norketamine” Shafiq Ur Rahman, Qiang Hao, Kaiwu He, Yumeng Li, Xifei Yang, Tao Ye, Tahir Ali, Qiang Zhou, Shupeng Li, Proteomics – Clinical Applications, 2020, https://doi.org/10.1002/prca.201900094
Abstract: Depression is a major disabling psychiatric disorder, causes severe financial burden and social consequences worldwide. Recently, (2R, 6R)-hydroxynorketamine (HNK), a metabolite of ketamine, showed strong antidepressant effects through an N-methyl-D aspartate (NMDA) antagonizing independent mechanism. In the current study we tried to identify the potential intracellular molecules and pathways that might be involved in different therapeutic effects underlying HNK as compared to NMDA antagonist MK-801.
10. “Total Synthesis of Dysoxylactam A” Mingze Yang, Wenquan Peng, Yian Guo, Tao Ye Lett. 2020, 22, 1776-9
Abstract: The total synthesis of a potent multi-drug-resistant reverser, dysoxylacatam A (1), was achieved in a highly eﬃcient and stereocontrolled fashion. The highlights of the strategy enlisted an iterative combination of lithiation−borylation tactics including Aggarwal homologation and Matteson homologation, Brown crotylation, Krische allylation, and ring-closing metathesis to forge the macrocycle.
11. “Reductase of Mutanobactin Synthetase Triggers Sequential C−C Macrocyclization, C−S Bond Formation, and C−C Bond Cleavage” Min Wang, Zhoujie Xie, Shoubin Tang, Ee Ling Chang, Yue Tang, Zhengyan Guo, Yinglu Cui, Bian Wu, Tao Ye, Yihua Chen Lett. 2020, 22, 960-4
Abstract: Mutanobactins (MUBs) and their congeners that contain a macrocycle and/or a thiazepane ring are lipopeptides from Streptococcus mutans, a major causative agent of dental caries. Here we show that the C-terminal reductase domain of MubD releases the lipohexapeptide intermediates in an aldehyde form, which enables a spontaneous C−C macrocyclization. In the presence of a thiol group, the macrocyclized MUBs can further undergo spontaneous C−S bond formation and C−C bond cleavage to generate diverse MUB congeners.