Synthesis and Glycosidase Inhibition of Australine and Its Fluorinated Derivatives

Li, Yi-Xian; Shimada, Yasuhiro; Sato, Kasumi; Kato, Atsushi; Zhang, Wei; Jia, Yue‐Mei; Fleet, George W. J.; Xiao, Min; Yu, Chu‐Yi

doi:10.1021/ol503728e

Cited by 44 publications

(20 citation statements)

References 62 publications

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“…According to the ring substitution and saturation of the compound, alkaloids also show biological activities in glycosidase inhibition, pulmonary hypertension, and hepatotoxicity, being a very attractive and challenging target for synthetic chemists to develop new methodologies …”

Section: Introductionsupporting

confidence: 55%

Elucidating the mass spectrum of the retronecine alkaloid using DFT calculations

et al. 2018

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Pyrrolizidine alkaloids are natural molecules playing important roles in different biochemical processes in nature and in humans. In this work, the electron ionization mass spectrum of retronecine, an alkaloid molecule found in plants, was investigated computationally. Its mass spectrum can be characterized by three main fragment ions having the following m/z ratios: 111, 94, and 80. In order to rationalize the mass spectrum, minima and transition state geometries were computed using density functional theory. It was showed that the dissociation process includes an aromatization of the originally five-membered ring of retronecine converted into a six-membered ring compound. A fragmentation pathway mechanism involving dissociation activation barriers that are easily overcome by the initial ionization energy was found. From the computed quantum chemical geometric, atomic charges, and energetic parameters, the abundance of each ion in the mass spectrum of retronecine was discussed.

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Section: Introductionsupporting

confidence: 55%

Elucidating the mass spectrum of the retronecine alkaloid using DFT calculations

et al. 2018

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“…Deacetylation of both the N ‐ and O ‐acetyl groups of 10 by using Na 2 CO 3 in MeOH gave primary alcohol 11 in 97 % yield in 4 h, which upon exposure to DMSO and Ac 2 O resulted in facile oxidation14 to give aldehyde 12 in 85 % yield; this aldehyde was stable enough to be purified by column chromatography and was characterized thoroughly. Initially, zinc‐mediated allylation of aldehyde 12 was attempted 15,16. However, the reaction was found to be extremely slow and did not go to completion even after 24 h at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Hybrid Conducting Biofilm with Built‐in Bacteria for High‐Performance Microbial Fuel Cells

Zhao

Ding

et al. 2015

ChemElectroChem

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Efficiently transportinge xtracellulare lectrons from microbial biofilms to the electrodes is challenging and criticali na chieving high-performance microbial fuel cells (MFCs). In this work, we develop as imple and effective method to fabricate hybrid electroactive biofilms by inserting bacteria into graphenecarbon-nanotube (G-CNT) networks (namely,G -CNT-biofilm) as an anode for MFCs. This novel architecture greatlye nhances direct extracellular electron transfer between Shewanella oneidensis and the electrode, due to strong adhesion of the hybrid conducting biofilm onto the anode surface, as well as the large surface area of graphene and the highc onductivity of CNTs. Ac urrent density of 120 mAcm À2 and am aximum power density of 97.9 mWcm À2 are obtained in the MFC with the hybrid biofilm anode, which is significantly highert han those of an aturallyg rowing biofilm anode (20 mAcm À2 and 6.5 mWcm À2 ).Electroactive microorganisms, organized as as tructured community (as biofilm) grown or enriched at the anode, have potential applicationsi nb ioelectrochemical systems( BESs), such as microbial fuel cells (MFCs)a nd electrolysis cells (ECs). For example,s uch systemsa re employed in energy generation and simultaneous wastewatert reatment. [1] However,t he relatively low power density in such BESs, mainly caused by poor extracellular electron transfer (EET), remains one of the main obstacles for their use in practical applications. [2] Generally,E ET from bacteria to electrode can occur via two mechanisms:1 )outermembrane cytochromes and conductive nanowires, and 2) mediated electron shuttles. [3] It is believed that EET efficiency is one of the key steps in determining the performance of BESs. Thus, how to dramatically enhance the EET is an important topic forBESs.As one family member of BESs, MFCs also employ electroactive microbial biofilms as biocatalysts to oxidizec omplex organic matter and to convert this chemical energy into electrical current. [4] Thus, the biofilm-based anode,s erving as as olid extracellular electron acceptor, has been considered as the heart of the MFC. [5] To emphasizei ts importance,s everal approaches have been explored to improve the properties of anodesf or facilitating EET processes. [6] For example, av ariety of electrode materials with high specific surface areas have been used, including stainless steel foam, three-dimensional (3D) macroporous electrodes and graphene-based materials. [7] Although these materials are desirable for the attachment of bacterialc ells, the number of cells formed on electrode surface remains ab ig challenge. It is thus highly desirable and important to develop simple and efficient strategies for large amountsofb acterial cells to adhere to the anode surface.Herein, we present as imple and effective methodt oc onstruct an ew architecture of highly electroactive hybrid biofilm, which is composed of ag raphene-carbon-nanotube( G-CNT) network with built-in bacteria (denoted as G-CNT-biofilm)a s an anode for MFCs (Scheme 1). Graphene oxide (GO...

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“…According to the research of Stütz et al6b and our previous study,5c hydroxyl groups on the DMDP moiety are important for interaction of the molecule with enzymes, and should remain intact in structure modification. Based on that assumption, we recently extended our studies to australine and L ‐homoDMDP, and found that fluorination at the C‐7 position of australine enhanced inhibition against α‐glucosidase,5f whereas replacement of side chain hydroxyl groups with fluoride in L ‐homoDMDP derivatives did not show any significant influence on α‐glucosidase inhibition 5g. The above results promoted our study of radicamines, which are a special class of DMDP related iminosugars in which aryl groups constitute their side chains.…”

Section: Introductionmentioning

confidence: 86%

Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition

Iwaki

Kato

et al. 2016

Eur J Org Chem

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Synthesis and Glycosidase Inhibition of Australine and Its Fluorinated Derivatives

Cited by 44 publications

References 62 publications

Elucidating the mass spectrum of the retronecine alkaloid using DFT calculations

Elucidating the mass spectrum of the retronecine alkaloid using DFT calculations

Hybrid Conducting Biofilm with Built‐in Bacteria for High‐Performance Microbial Fuel Cells

Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition

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