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Article ; Online: Total Synthesis of Pseudouridimycin.

Wang, Xu-Kun / Jia, Yue-Mei / Li, Yi-Xian / Yu, Chu-Yi

Organic letters

2022 Volume 24, Issue 2, Page(s) 511–515

Abstract: Pseudouridimycin ( ...

Abstract	Pseudouridimycin (
MeSH term(s)	Nucleosides/analogs & derivatives
Chemical Substances	Nucleosides ; pseudouridimycin
Language	English
Publishing date	2022-01-10
Publishing country	United States
Document type	Journal Article
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.1c03914
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Article: Application of electroacupuncture in the prevention of low anterior resection syndrome after rectal cancer surgery.

Xu, Lu-Lu / Xiang, Neng-Jun / Cheng, Tian-Cheng / Li, Yi-Xian / Chen, Peng / Jiang, Zhi-Wei / Liu, Xin-Xin

World journal of gastrointestinal surgery

2024 Volume 15, Issue 12, Page(s) 2765–2773

Abstract: Background: Low anterior resection syndrome (LARS) is one of the common postoperative complications in patients with rectal cancer, which seriously affects their postoperative recovery and quality of life (QoL). Electroacupuncture therapy is one of the ... ...

Abstract	Background: Low anterior resection syndrome (LARS) is one of the common postoperative complications in patients with rectal cancer, which seriously affects their postoperative recovery and quality of life (QoL). Electroacupuncture therapy is one of the characteristic therapies of traditional Chinese medicine. There are few reports on the prevention and treatment of LARS by electroacupuncture therapy. Aim: To explore the clinical effectiveness of electroacupuncture in managing rectal cancer patients with postoperative LARS. Methods: A total of 50 patients with LARS after rectal cancer surgery were retrospectively selected as the research subjects. According to the treatment methods, they were divided into an observation group ( Results: The experimental group showed considerably enhanced LARSS scores compared to those in the control group after four weeks of treatment. In the first week, second week, and fourth week, the LARSS score and Wexner anal incontinence scale score decreased, and the Xu Zhong method five-item 10-point scale score increased, with significant differences ( Conclusion: Electroacupuncture positively impacted LARS following rectal cancer surgery, effectively improving clinical symptoms and anal pressure indicators and patients' standard of life.
Language	English
Publishing date	2024-01-11
Publishing country	United States
Document type	Journal Article
ZDB-ID	2573700-4
ISSN	1948-9366
ISSN	1948-9366
DOI	10.4240/wjgs.v15.i12.2765
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Article: Total Synthesis of Pseudouridimycin

Wang, Xu-Kun / Jia, Yue-Mei / Li, Yi-Xian / Yu, Chu-Yi

Organic letters. 2022 Jan. 10, v. 24, no. 2

2022

Abstract: Pseudouridimycin (1), a potent antibiotic against both Gram-positive and Gram-negative bacteria including multi-drug-resistant strains with a new mode of action isolated from Streptomyces sp., was synthesized by a convergent strategy from 5′-amino- ... ...

Abstract	Pseudouridimycin (1), a potent antibiotic against both Gram-positive and Gram-negative bacteria including multi-drug-resistant strains with a new mode of action isolated from Streptomyces sp., was synthesized by a convergent strategy from 5′-amino-pseudouridine 5 and N-hydroxy-dipeptide 26 in 23% total yield. The key intermediate 26 was synthesized by hydroxylaminolysis of the nitrone derived from glutamine and subsequent glycylation with glycine chloride. The synthetic method provides an efficient and practical way for the synthesis of N-hydroxylated peptidyl nucleoside.
Keywords	Streptomyces ; antibiotics ; chlorides ; glutamine ; mechanism of action ; multiple drug resistance ; nucleosides
Language	English
Dates of publication	2022-0110
Size	p. 511-515.
Publishing place	American Chemical Society
Document type	Article
ISSN	1523-7052
DOI	10.1021/acs.orglett.1c03914
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Article ; Online: Design, synthesis and glycosidase inhibition of DAB derivatives with C-4 peptide and dipeptide branches.

Zi, Dong / Shimadate, Yuna / Wang, Jun-Zhe / Kato, Atsushi / Li, Yi-Xian / Jia, Yue-Mei / Fleet, George W J / Yu, Chu-Yi

Organic & biomolecular chemistry

2023 Volume 21, Issue 13, Page(s) 2729–2741

Abstract: A series of DAB-peptide and DAB-dipeptide derivatives were synthesized from D-tartrate-derived nitrone 18. The DAB peptides 16 are derivatives ... ...

Abstract	A series of DAB-peptide and DAB-dipeptide derivatives were synthesized from D-tartrate-derived nitrone 18. The DAB peptides 16 are derivatives of
MeSH term(s)	Animals ; Cattle ; Glycoside Hydrolases ; Molecular Docking Simulation ; Dipeptides ; C-Peptide ; beta-Galactosidase ; Structure-Activity Relationship ; Molecular Structure
Chemical Substances	Glycoside Hydrolases (EC 3.2.1.-) ; Dipeptides ; C-Peptide ; beta-Galactosidase (EC 3.2.1.23)
Language	English
Publishing date	2023-03-29
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/d3ob00097d
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Article ; Online: C-6 fluorinated casuarines as highly potent and selective amyloglucosidase inhibitors: Synthesis and structure-activity relationship study.

Li, Yi-Xian / Wang, Jun-Zhe / Shimadate, Yuna / Kise, Maki / Kato, Atsushi / Jia, Yue-Mei / Fleet, George W J / Yu, Chu-Yi

European journal of medicinal chemistry

2022 Volume 244, Page(s) 114852

Abstract: A series of C-6 fluorinated casuarine derivatives have been synthesized via organocatalytic stereoselective α-fluorination of iminosugar-based aldehydes or direct nucleophilic fluorination of polyhydroxylated pyrrolizidines. Glycosidase assays against ... ...

Abstract	A series of C-6 fluorinated casuarine derivatives have been synthesized via organocatalytic stereoselective α-fluorination of iminosugar-based aldehydes or direct nucleophilic fluorination of polyhydroxylated pyrrolizidines. Glycosidase assays against various glycosidases allowed systematic structure-activity relationship (SAR) study using molecular docking calculations. Introduction of fluorine atom(s) at C-6 position removed the trehalase and maltase inhibitory activities of all casuarine derivatives, and greatly increased their specificity towards amyloglucosidase. Inhibition of the fluorinated casuarines depended on the configuration of C-6 fluorine, of which 6-deoxy-6-epi-6-fluoro-casuarine (24) was found approximately 40-fold potent than its parent compound 6-epi-casuarine (2) as a potent and specific inhibitor of amyloglucosidase. Molecular docking calculations showed that replacement of the C-6 hydroxyls by fluorine atom(s) removed the original interactions with trehalase, but helped to reinforce the binding with amyloglucosidase via newly established fluorine related hydrogen bonding or untypical anion-π interactions. To further investigate the quantitative SARs of casuarine derivatives, the CoMFA and CoMSIA models on amyloglucosidase were established, indicating the dominating effect of electrostatic field in amyloglucosidase inhibition. The 3D-QSAR models were validated to be reliable and can be used for further optimization of casuarine-related iminosugars, as well as design and development of anti-diabetic and immunomodulatory drugs.
MeSH term(s)	Molecular Docking Simulation ; Glucan 1,4-alpha-Glucosidase/metabolism ; Trehalase/metabolism ; Fluorine ; Quantitative Structure-Activity Relationship ; Structure-Activity Relationship ; Glycoside Hydrolases
Chemical Substances	casuarine ; Glucan 1,4-alpha-Glucosidase (EC 3.2.1.3) ; Trehalase (EC 3.2.1.28) ; Fluorine (284SYP0193) ; Glycoside Hydrolases (EC 3.2.1.-)
Language	English
Publishing date	2022-10-21
Publishing country	France
Document type	Journal Article
ZDB-ID	188597-2
ISSN	1768-3254 ; 0009-4374 ; 0223-5234
ISSN (online)	1768-3254
ISSN	0009-4374 ; 0223-5234
DOI	10.1016/j.ejmech.2022.114852
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Article ; Online: Diastereoselective Synthesis, Glycosidase Inhibition, and Docking Study of C-7-Fluorinated Casuarine and Australine Derivatives.

Li, Yi-Xian / Wang, Jun-Zhe / Shimadate, Yuna / Kise, Maki / Kato, Atsushi / Jia, Yue-Mei / Fleet, George W J / Yu, Chu-Yi

The Journal of organic chemistry

2022 Volume 87, Issue 11, Page(s) 7291–7307

Abstract: C-7-fluorinated derivatives of two important polyhydroxylated pyrrolizidines, casuarine and australine, were synthesized with organocatalytic stereoselective α-fluorination of aldehydes as the key step. The strategy is extensively applicable to some ... ...

Abstract	C-7-fluorinated derivatives of two important polyhydroxylated pyrrolizidines, casuarine and australine, were synthesized with organocatalytic stereoselective α-fluorination of aldehydes as the key step. The strategy is extensively applicable to some synthetically challenging fluorinated iminosugars and carbohydrates. The docking studies indicated that the potent inhibitions of trehalase and amyloglucosidase by the fluorinated polyhydroxylated pyrrolizidines are due to the interaction modes dominated by fluorine atoms in these iminosugars with the amino acids' residues of the corresponding enzymes. Steady interactions were established between the C-7 fluoride and a hydrophobic pocket in amyloglucosidase by untypical anion-π interactions. These unexpected docking modes and related structure-activity relationship studies emphasize the value of fluorination in the design of polyhydroxylated pyrrolizidine glycosidase inhibitors.
MeSH term(s)	Alkaloids ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; Glucan 1,4-alpha-Glucosidase ; Glycoside Hydrolases ; Pyrroles ; Pyrrolizidine Alkaloids
Chemical Substances	Alkaloids ; Enzyme Inhibitors ; Pyrroles ; Pyrrolizidine Alkaloids ; casuarine ; australine (118396-02-4) ; Glycoside Hydrolases (EC 3.2.1.-) ; Glucan 1,4-alpha-Glucosidase (EC 3.2.1.3)
Language	English
Publishing date	2022-05-18
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.2c00485
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Article ; Online: trans, trans-2-C-Aryl-3,4-dihydroxypyrrolidines as potent and selective β-glucosidase inhibitors: Pharmacological chaperones for Gaucher disease.

Wang, Jun-Zhe / Shimadate, Yuna / Kise, Maki / Kato, Atsushi / Jia, Yue-Mei / Li, Yi-Xian / Fleet, George W J / Yu, Chu-Yi

European journal of medicinal chemistry

2022 Volume 238, Page(s) 114499

Abstract: Enantiomeric series of C-4 hydroxymethyl depleted DAB and LAB derivatives (trans, trans-2-C-aryl-3,4-dihydroxypyrrolidines), designed as β-glucosidase inhibitors by molecular docking calculations, have been synthesized in 2 steps from l- and d-tartaric ... ...

Abstract	Enantiomeric series of C-4 hydroxymethyl depleted DAB and LAB derivatives (trans, trans-2-C-aryl-3,4-dihydroxypyrrolidines), designed as β-glucosidase inhibitors by molecular docking calculations, have been synthesized in 2 steps from l- and d-tartaric acid derived enantiomeric cyclic nitrones 29L and 29D, respectively. Both series of C-4 hydroxymethyl depleted DAB and LAB derivatives 28Da-e and 28La-e, which are structurally trans, trans-2-C-aryl-3,4-dihydroxypyrrolidines, were potent and selective human lysosome acid β-glucosidase (GCase) inhibitors, of which 28Dd and 28Ld with C-4 biphenyls showed the highest potency relative to other compounds of the same series. The work provided a series of pyrrolidine-type potent and selective GCase inhibitors with minimal hydroxyl substitutions and synthetic procedures. Structure-activity relationship study revealed not only the rationality of hydrophobic and aromatic properties of the binding sites in GCase, but also the great potential of pyrrolidine family in development of new GCase inhibitors with minimized undesirable side effects. The results indicate a strategy for the development of drugs for the treatment of related diseases targeting acid β-glucosidase, such as Gaucher disease and Parkinson's disease.
MeSH term(s)	Enzyme Inhibitors/chemistry ; Gaucher Disease/drug therapy ; Glucosylceramidase ; Humans ; Molecular Docking Simulation ; Pyrrolidines/pharmacology ; Pyrrolidines/therapeutic use ; beta-Glucosidase
Chemical Substances	3,4-dihydroxypyrrolidine ; Enzyme Inhibitors ; Pyrrolidines ; beta-Glucosidase (EC 3.2.1.21) ; Glucosylceramidase (EC 3.2.1.45)
Language	English
Publishing date	2022-05-29
Publishing country	France
Document type	Journal Article
ZDB-ID	188597-2
ISSN	1768-3254 ; 0009-4374 ; 0223-5234
ISSN (online)	1768-3254
ISSN	0009-4374 ; 0223-5234
DOI	10.1016/j.ejmech.2022.114499
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Article: Diastereoselective Synthesis, Glycosidase Inhibition, and Docking Study of C-7-Fluorinated Casuarine and Australine Derivatives

Li, Yi-Xian / Wang, Jun-Zhe / Shimadate, Yuna / Kise, Maki / Kato, Atsushi / Jia, Yue-Mei / Fleet, George W. J. / Yu, Chu-Yi

Journal of organic chemistry. 2022 May 18, v. 87, no. 11

2022

Abstract	C-7-fluorinated derivatives of two important polyhydroxylated pyrrolizidines, casuarine and australine, were synthesized with organocatalytic stereoselective α-fluorination of aldehydes as the key step. The strategy is extensively applicable to some synthetically challenging fluorinated iminosugars and carbohydrates. The docking studies indicated that the potent inhibitions of trehalase and amyloglucosidase by the fluorinated polyhydroxylated pyrrolizidines are due to the interaction modes dominated by fluorine atoms in these iminosugars with the amino acids’ residues of the corresponding enzymes. Steady interactions were established between the C-7 fluoride and a hydrophobic pocket in amyloglucosidase by untypical anion−π interactions. These unexpected docking modes and related structure–activity relationship studies emphasize the value of fluorination in the design of polyhydroxylated pyrrolizidine glycosidase inhibitors.
Keywords	catalytic activity ; diastereoselective synthesis ; fluorides ; fluorine ; hydrophobicity ; imino sugars ; organic chemistry ; stereoselectivity ; structure-activity relationships ; trehalase
Language	English
Dates of publication	2022-0518
Size	p. 7291-7307.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.2c00485
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Article ; Online: Specific calcineurin isoforms are involved in Drosophila toll immune signaling.

Li, Yi-Xian / Dijkers, Pascale F

Journal of immunology (Baltimore, Md. : 1950)

2014 Volume 194, Issue 1, Page(s) 168–176

Abstract: Because excessive or inadequate responses can be detrimental, immune responses to infection require appropriate regulation. Networks of signaling pathways establish versatility of immune responses. Drosophila melanogaster is a powerful model organism for ...

Abstract	Because excessive or inadequate responses can be detrimental, immune responses to infection require appropriate regulation. Networks of signaling pathways establish versatility of immune responses. Drosophila melanogaster is a powerful model organism for dissecting conserved innate immune responses to infection. For example, the Toll pathway, which promotes activation of NF-κB transcription factors Dorsal/Dorsal-related immune factor (Dif), was first identified in Drosophila. Together with the IMD pathway, acting upstream of NF-κB transcription factor Relish, these pathways constitute a central immune signaling network. Inputs in these pathways contribute to specific and appropriate responses to microbial insults. Relish activity during infection is modulated by Ca(2+)-dependent serine/threonine phosphatase calcineurin, an important target of immunosuppressants in transplantation biology. Only one of the three Drosophila calcineurin isoforms, calcineurin A1, acts on Relish during infection. However, it is not known whether there is a role for calcineurin in Dorsal/Dif immune signaling. In this article, we demonstrate involvement of specific calcineurin isoforms, protein phosphatase at 14D (Pp2B-14D)/calcineurin A at 14F (CanA-14F), in Toll-mediated immune signaling. These isoforms do not affect IMD signaling. In cell culture, pharmacological inhibition of calcineurin or RNA interference against homologous calcineurin isoforms Pp2B-14D/CanA-14F, but not against isoform calcineurin A1, decreased Toll-dependent Dorsal/Dif activity. A Pp2B-14D gain-of-function transgene promoted Dorsal nuclear translocation and Dorsal/Dif activity. In vivo, Pp2B-14D/CanA-14F RNA interference attenuated the Dorsal/Dif-dependent response to infection without affecting the Relish-dependent response. Altogether, these data identify a novel input, calcineurin, in Toll immune signaling and demonstrate involvement of specific calcineurin isoforms in Drosophila NF-κB signaling.
MeSH term(s)	Animals ; Calcineurin/genetics ; Calcineurin/immunology ; Cell Line ; DNA-Binding Proteins/immunology ; Drosophila Proteins/immunology ; Drosophila melanogaster/immunology ; Drosophila melanogaster/microbiology ; Green Fluorescent Proteins/genetics ; Infection/immunology ; NF-kappa B/immunology ; Nuclear Proteins/immunology ; Phosphoproteins/immunology ; Protein Isoforms/genetics ; Protein Isoforms/immunology ; RNA Interference ; RNA, Small Interfering ; Signal Transduction/immunology ; Tacrolimus/pharmacology ; Toll-Like Receptors/immunology ; Transcription Factors/immunology
Chemical Substances	DNA-Binding Proteins ; Dif protein, Drosophila ; Drosophila Proteins ; NF-kappa B ; Nuclear Proteins ; Phosphoproteins ; Protein Isoforms ; RNA, Small Interfering ; Rel protein, Drosophila ; Tl protein, Drosophila ; Toll-Like Receptors ; Transcription Factors ; dl protein, Drosophila ; Green Fluorescent Proteins (147336-22-9) ; Calcineurin (EC 3.1.3.16) ; Tacrolimus (WM0HAQ4WNM)
Language	English
Publishing date	2014-11-26
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	3056-9
ISSN	1550-6606 ; 0022-1767 ; 1048-3233 ; 1047-7381
ISSN (online)	1550-6606
ISSN	0022-1767 ; 1048-3233 ; 1047-7381
DOI	10.4049/jimmunol.1401080
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Article ; Online: Design and synthesis of iso-

Yang, Lin-Feng / Zhang, Ming / Shimadate, Yuna / Kato, Atsushi / Hou, Tian-Yang Liu / Li, Yi-Xian / Jia, Yue-Mei / Fleet, George W J / Yu, Chu-Yi

Organic & biomolecular chemistry

2023 Volume 21, Issue 16, Page(s) 3453–3464

Abstract: A series of iso- ...

Abstract	A series of iso-
MeSH term(s)	alpha-Glucosidases/metabolism ; Structure-Activity Relationship ; Molecular Docking Simulation ; Glycoside Hydrolase Inhibitors/pharmacology ; Glycoside Hydrolases ; Molecular Structure
Chemical Substances	alpha-Glucosidases (EC 3.2.1.20) ; Glycoside Hydrolase Inhibitors ; Glycoside Hydrolases (EC 3.2.1.-)
Language	English
Publishing date	2023-04-26
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/d3ob00404j
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