LIVIVO - Search results -

Search results

Result 1 - 10 of total 49

Search options

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
Database	MEDical Literature Analysis and Retrieval System OnLINE

Order via subito

This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.

Inter-library loan at ZB MED

Your chosen title can be delivered directly to ZB MED Cologne location if you are registered as a user at ZB MED Cologne.

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
Database	NAL-Catalogue (AGRICOLA)

Order via subito

Inter-library loan at ZB MED

Your chosen title can be delivered directly to ZB MED Cologne location if you are registered as a user at ZB MED Cologne.

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
Database	MEDical Literature Analysis and Retrieval System OnLINE

Order via subito

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
Database	MEDical Literature Analysis and Retrieval System OnLINE

In stock of ZB MED Cologne/Königswinter

Zs.B 784: Show issues

Location:
Je nach Verfügbarkeit (siehe Angabe bei Bestand)
bis Jg. 2021: Bestellungen von Artikeln über das Online-Bestellformular
ab Jg. 2022: Lesesaal (EG)

Order via subito

Details ▾
- See ZB MED holdings
- Order with fees

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
Database	MEDical Literature Analysis and Retrieval System OnLINE

In stock of ZB MED Cologne/Königswinter

Zs.A 4473: Show issues

Location:
Je nach Verfügbarkeit (siehe Angabe bei Bestand)
bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
Jg. 1995 - 2021: Lesesall (2.OG)
ab Jg. 2022: Lesesaal (EG)

Order via subito

Details ▾
- See ZB MED holdings
- Order with fees

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
Database	MEDical Literature Analysis and Retrieval System OnLINE

In stock of ZB MED Cologne/Königswinter

Zs.B 784: Show issues

Location:
Je nach Verfügbarkeit (siehe Angabe bei Bestand)
bis Jg. 2021: Bestellungen von Artikeln über das Online-Bestellformular
ab Jg. 2022: Lesesaal (EG)

Order via subito

Details ▾
- See ZB MED holdings
- Order with fees

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
Database	NAL-Catalogue (AGRICOLA)

In stock of ZB MED Bonn / Germany

Z 4' 49/42: Show issues
Z 7.1: Show issues

Order via subito

Inter-library loan at ZB MED

Your chosen title can be delivered directly to ZB MED Cologne location if you are registered as a user at ZB MED Cologne.

Details ▾
- See ZB MED holdings
- Order with fees

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
Database	MEDical Literature Analysis and Retrieval System OnLINE

Order via subito

Article ; Online: Stereocomplementary synthesis of casuarine and its 6-

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

Organic & biomolecular chemistry

2021 Volume 19, Issue 43, Page(s) 9410–9420

Abstract: Four diastereomers belonging to the family of casuarines, including casuarine (1), 6- ...

Abstract	Four diastereomers belonging to the family of casuarines, including casuarine (1), 6-
Language	English
Publishing date	2021-11-10
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/d1ob01725j
Database	MEDical Literature Analysis and Retrieval System OnLINE

Order via subito

Article ; Online: Nanomolar β-glucosidase and β-galactosidase inhibition by enantiomeric α-1-C-alkyl-1,4-dideoxy-1,4-imino-arabinitol derivatives.

Zi, Dong / Song, Ying-Ying / Lu, Tian-Tian / Kise, Maki / Kato, Atsushi / Wang, Jun-Zhe / Jia, Yue-Mei / Li, Yi-Xian / Fleet, George W J / Yu, Chu-Yi

European journal of medicinal chemistry

2022 Volume 247, Page(s) 115056

Abstract: A series of α-1-C-alkyl DAB (1,4-dideoxy-1,4-imino-d-arabinitol) and LAB (1,4-dideoxy-1,4-imino-l-arabinitol) derivatives with aryl substituents have been designed as analogues of broussonetine W (12), and assayed as glycosidase inhibitors. While the ... ...

Abstract	A series of α-1-C-alkyl DAB (1,4-dideoxy-1,4-imino-d-arabinitol) and LAB (1,4-dideoxy-1,4-imino-l-arabinitol) derivatives with aryl substituents have been designed as analogues of broussonetine W (12), and assayed as glycosidase inhibitors. While the inhibition spectrum of α-1-C-alkyl DAB derivative 16 showed a good correlation to that of broussonetine W (12), introduction of substituents on the terminal aryl (17a-f) or hydroxyl groups at C-1' position of the alkyl chains (18a-e) decreased their α-glucosidase inhibitions but greatly improved their inhibitions of bovine liver β-glucosidase and β-galactosidase. Furthermore, epimerization of C-1' configurations of compounds 18a-e clearly lowered their inhibition potency of bovine liver β-glucosidase and β-galactosidase. Notably, some of the α-1-C-alkyl DAB derivatives were also found to have potent human lysosome β-glucosidase inhibitions. In contrast, enantiomers of compounds 18a-e and 1'-epi-18a-e generally showed increased α-glucosidase inhibitions, but sharply decreased bovine liver β-glucosidase and β-galactosidase inhibitions. Molecular docking calculations unveiled the novel two set of binding modes for each series of compounds; introduction of C-1' hydroxyl altered the conformations of the pyrrolidine rings and orientation of their long chains, resulting in improved accommodation in the hydrophobic grooves. The compounds reported herein are very potent β-glucosidase and β-galactosidase inhibitions with novel binding mode; and the structure-activity relationship provides guidance for design and development of more pyrrolidine pharmacological chaperones for lysosomal storage diseases.
MeSH term(s)	Animals ; Cattle ; Humans ; alpha-Glucosidases/metabolism ; beta-Galactosidase ; beta-Glucosidase ; Enzyme Inhibitors/pharmacology ; Enzyme Inhibitors/chemistry ; Molecular Docking Simulation ; Pyrrolidines/pharmacology ; Structure-Activity Relationship
Chemical Substances	alpha-Glucosidases (EC 3.2.1.20) ; arabitol (YFV05Y57M9) ; beta-Galactosidase (EC 3.2.1.23) ; beta-Glucosidase (EC 3.2.1.21) ; broussonetine W ; Enzyme Inhibitors ; Pyrrolidines ; 1,4-dideoxy-1,4-iminoarabinitol (100937-53-9)
Language	English
Publishing date	2022-12-28
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.2022.115056
Database	MEDical Literature Analysis and Retrieval System OnLINE

In stock of ZB MED Cologne/Königswinter

Zs.B 784: Show issues

Location:
Je nach Verfügbarkeit (siehe Angabe bei Bestand)
bis Jg. 2021: Bestellungen von Artikeln über das Online-Bestellformular
ab Jg. 2022: Lesesaal (EG)

Order via subito

Details ▾
- See ZB MED holdings
- Order with fees

To top

More links

Kategorien

Order via subito

Inter-library loan at ZB MED

More links

Kategorien

Order via subito

Inter-library loan at ZB MED

More links

Kategorien

Order via subito

More links

Kategorien

In stock of ZB MED Cologne/Königswinter

Order via subito

More links

Kategorien

In stock of ZB MED Cologne/Königswinter

Order via subito

More links

Kategorien

In stock of ZB MED Cologne/Königswinter

Order via subito

More links

Kategorien

In stock of ZB MED Bonn / Germany

Order via subito

Inter-library loan at ZB MED

More links

Kategorien

Order via subito

More links

Kategorien

Order via subito

More links

Kategorien

In stock of ZB MED Cologne/Königswinter

Order via subito