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Article ; Online: Synthesis of 4'-Thionucleoside Analogues Bearing a C2' Stereogenic All-Carbon Quaternary Center.

Eymard, Carla / Manchoju, Amarender / Almazloum, Abir / Dostie, Starr / Prévost, Michel / Nemer, Mona / Guindon, Yvan

2024 Volume 29, Issue 7

Abstract: The design of novel 4'-thionucleoside analogues bearing a C2' stereogenic all-carbon quaternary center is described. The synthesis involves a highly diastereoselective Mukaiyama aldol reaction, and a diastereoselective radical-based vinyl group transfer ... ...

Abstract	The design of novel 4'-thionucleoside analogues bearing a C2' stereogenic all-carbon quaternary center is described. The synthesis involves a highly diastereoselective Mukaiyama aldol reaction, and a diastereoselective radical-based vinyl group transfer to generate the all-carbon stereogenic C2' center, along with different approaches to control the selectivity of the
MeSH term(s)	Cyclization ; Glycosylation ; Carbon ; Cardiac Glycosides ; Thionucleosides
Chemical Substances	Carbon (7440-44-0) ; Cardiac Glycosides ; Thionucleosides
Language	English
Publishing date	2024-04-06
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules29071647
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Article ; Online: Sialyl Lewis

Belouin, Audrey / Simard, Ryan D / Joyal, Mathieu / Maharsy, Wael / Lau, Alice / Prévost, Michel / Nemer, Mona / Guindon, Yvan

Bioorganic & medicinal chemistry

2023 Volume 98, Page(s) 117553

Abstract: Neutrophil binding to vascular P- and E-selectin is the rate-limiting step in the recruitment of immune cells to sites of inflammation. Many diseases, including sickle cell anemia, post-myocardial infarction reperfusion injury, and acute respiratory ... ...

Abstract	Neutrophil binding to vascular P- and E-selectin is the rate-limiting step in the recruitment of immune cells to sites of inflammation. Many diseases, including sickle cell anemia, post-myocardial infarction reperfusion injury, and acute respiratory distress syndrome are characterized by dysregulated inflammation. We have recently reported sialyl Lewis
MeSH term(s)	Humans ; P-Selectin/metabolism ; E-Selectin/metabolism ; Tartrates ; Sialyl Lewis X Antigen ; Oligosaccharides/chemistry ; Binding Sites ; Carbon ; Inflammation ; Cell Adhesion
Chemical Substances	P-Selectin ; E-Selectin ; tartaric acid (W4888I119H) ; Tartrates ; Sialyl Lewis X Antigen ; Oligosaccharides ; Carbon (7440-44-0)
Language	English
Publishing date	2023-12-09
Publishing country	England
Document type	Journal Article
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2023.117553
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Article ; Online: Diastereoselective Radical Hydrogen Transfer Reactions using N-Heterocyclic Carbene Boranes.

Tambutet, Guillaume / Guindon, Yvan

The Journal of organic chemistry

2016 Volume 81, Issue 22, Page(s) 11427–11431

Abstract: Reported herein are the first diastereoselective and Lewis acid-mediated radical reactions of N-heterocyclic carbene (NHC) boranes. We applied these reactions to the synthesis of four propionate diastereoisomers combining an aldol reaction, followed by a ...

Abstract	Reported herein are the first diastereoselective and Lewis acid-mediated radical reactions of N-heterocyclic carbene (NHC) boranes. We applied these reactions to the synthesis of four propionate diastereoisomers combining an aldol reaction, followed by a stereoselective radical-based reduction in which the NHC borane serves as the hydrogen donor, thus obviating the use of tin-based reagents. The 2,3-syn isomer is obtained by combining an NHC-borane and a Lewis acid (MgBr
Language	English
Publishing date	2016-11-18
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.6b02066
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Article: Diastereoselective Radical Hydrogen Transfer Reactions using N-Heterocyclic Carbene Boranes

Tambutet, Guillaume / Guindon Yvan

Journal of organic chemistry. 2016 Nov. 18, v. 81, no. 22

2016

Abstract	Reported herein are the first diastereoselective and Lewis acid-mediated radical reactions of N-heterocyclic carbene (NHC) boranes. We applied these reactions to the synthesis of four propionate diastereoisomers combining an aldol reaction, followed by a stereoselective radical-based reduction in which the NHC borane serves as the hydrogen donor, thus obviating the use of tin-based reagents. The 2,3-syn isomer is obtained by combining an NHC-borane and a Lewis acid (MgBrâÂ·OEtâ), while using a reverse polarity strategy provides the 2,3-anti isomer.
Keywords	boranes ; carbenes ; chemical reactions ; diastereomers ; diastereoselectivity ; heterocyclic nitrogen compounds ; hydrogen ; Lewis acids ; organic chemistry ; propionic acid
Language	English
Dates of publication	2016-1118
Size	p. 11427-11431.
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%2Facs.joc.6b02066
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Article ; Online: Nucleotide Analogues Bearing a C2' or C3'-Stereogenic All-Carbon Quaternary Center as SARS-CoV-2 RdRp Inhibitors.

Manchoju, Amarender / Zelli, Renaud / Wang, Gang / Eymard, Carla / Oo, Adrian / Nemer, Mona / Prévost, Michel / Kim, Baek / Guindon, Yvan

Molecules (Basel, Switzerland)

2022 Volume 27, Issue 2

Abstract: The design of novel nucleoside triphosphate (NTP) analogues bearing an all-carbon quaternary center at C2' or C3' is described. The construction of this all-carbon stereogenic center involves the use of an intramoleculer photoredox-catalyzed reaction. ... ...

Abstract	The design of novel nucleoside triphosphate (NTP) analogues bearing an all-carbon quaternary center at C2' or C3' is described. The construction of this all-carbon stereogenic center involves the use of an intramoleculer photoredox-catalyzed reaction. The nucleoside analogues (NA) hydroxyl functional group at C2' was generated by diastereoselective epoxidation. In addition, highly enantioselective and diastereoselective Mukaiyama aldol reactions, diastereoselective
MeSH term(s)	Antiviral Agents/chemical synthesis ; Antiviral Agents/chemistry ; Antiviral Agents/pharmacology ; Carbon/chemistry ; Heterocyclic Compounds, 4 or More Rings/chemical synthesis ; Heterocyclic Compounds, 4 or More Rings/chemistry ; Heterocyclic Compounds, 4 or More Rings/pharmacology ; Nucleotides/chemical synthesis ; Nucleotides/chemistry ; Nucleotides/pharmacology ; RNA-Dependent RNA Polymerase/antagonists & inhibitors ; SARS-CoV-2/drug effects ; SARS-CoV-2/enzymology ; Stereoisomerism
Chemical Substances	Antiviral Agents ; Heterocyclic Compounds, 4 or More Rings ; Nucleotides ; Carbon (7440-44-0) ; RNA-Dependent RNA Polymerase (EC 2.7.7.48)
Language	English
Publishing date	2022-01-17
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules27020564
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Article ; Online: Synthesis of Sialyl Lewis

Simard, Ryan D / Joyal, Mathieu / Beaugrand, Thomas / Gauthier, Julien / Hardine, Elodie / Desriac, Axelle / Buffet, Charles-Henri / Prévost, Michel / Nemer, Mona / Guindon, Yvan

The Journal of organic chemistry

2023 Volume 88, Issue 15, Page(s) 10974–10985

Abstract: E- and P-selectins are adhesion proteins implicated in immune cell recruitment at sites of infection, making them important drug targets for diseases involving excessive and uncontrolled inflammation. In this study, we developed an efficient strategy to ... ...

Abstract	E- and P-selectins are adhesion proteins implicated in immune cell recruitment at sites of infection, making them important drug targets for diseases involving excessive and uncontrolled inflammation. In this study, we developed an efficient strategy to synthesize bicyclic galactopyranosides through a key stereoselective equatorial C4-propiolate addition and TMSCN axial C-glycosidation. The nitrile group can then be converted to the carboxyl and different bioisosteres at a late stage in the synthesis, allowing for various derivatizations to potentially enhance biological activity. The sialyl Lewis
MeSH term(s)	P-Selectin/chemistry ; P-Selectin/metabolism ; Sialyl Lewis X Antigen ; Endothelial Cells/metabolism ; Oligosaccharides/chemistry
Chemical Substances	P-Selectin ; Sialyl Lewis X Antigen ; Oligosaccharides
Language	English
Publishing date	2023-07-14
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.3c00956
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Article: Photoredox-Catalyzed Stereoselective Radical Reactions to Synthesize Nucleoside Analogues with a C2′-Stereogenic All-Carbon Quaternary Center

Becerril-Jiménez, Fabiola / Lussier, Tommy / Leblanc, Louis / Eymard, Carla / Dostie, Starr / Prévost, Michel / Guindon, Yvan

Journal of organic chemistry. 2019 Oct. 22, v. 84, no. 22

2019

Abstract: The design of novel nucleoside analogues bearing a C2′ all-carbon quaternary center is described. The construction of this all-carbon stereogenic center involves the use of photoredox catalysis to initiate an intramolecular attack of a silyl-tethered ... ...

Abstract	The design of novel nucleoside analogues bearing a C2′ all-carbon quaternary center is described. The construction of this all-carbon stereogenic center involves the use of photoredox catalysis to initiate an intramolecular attack of a silyl-tethered vinyl functionality on a tertiary radical. Density functional theory calculations were performed to explore the origin of the high syn diastereoselectivity obtained through the preferred 5-exo-trig cyclization mode. The intramolecular vinyl addition also enables the preparation of the complementary configuration of the C2′ all-carbon stereocenter when performed after lactonization.
Keywords	catalytic activity ; chemical structure ; density functional theory ; diastereoselectivity ; nucleosides ; organic compounds ; redox reactions
Language	English
Dates of publication	2019-1022
Size	p. 14795-14804.
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.9b02374
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Article: Diastereoselective Synthesis of Arabino- and Ribo-like Nucleoside Analogues Bearing a Stereogenic C3′ All-Carbon Quaternary Center

Lussier, Tommy / Manchoju, Amarender / Wang, Gang / Dostie, Starr / Foster, Scott / Mochirian, Philippe / Prévost, Michel / Guindon, Yvan

Journal of organic chemistry. 2019 Nov. 15, v. 84, no. 24

2019

Abstract: The synthesis of novel nucleoside analogues bearing a C3′ all-carbon quaternary center and a C2′-hydroxy substituent is described. The all-carbon stereogenic center was generated through an intramolecular 7-endo attack of a silyl-tethered allyl moiety on ...

Abstract	The synthesis of novel nucleoside analogues bearing a C3′ all-carbon quaternary center and a C2′-hydroxy substituent is described. The all-carbon stereogenic center was generated through an intramolecular 7-endo attack of a silyl-tethered allyl moiety on a tertiary radical using photoredox catalysis. Subsequent allylic oxidation and diastereoselective hydride reductions provided the hydroxy substituent at C2′, which then controls the stereoselective introduction of pyrimidine nucleobases on the corresponding furanose scaffold. Density functional theory (DFT) calculations provided insights into the origin of the high syn diastereoselectivity resulting from the radical cyclization. This original methodology grants access to a wide range of 1′,2′-cis and 1′,2′-trans arabino- and ribo-like analogues bearing an all-carbon quaternary center at C3′. These molecules are currently being tested for their antiviral and anticancer properties.
Keywords	antineoplastic activity ; catalytic activity ; cyclization reactions ; density functional theory ; diastereoselective synthesis ; diastereoselectivity ; hydrides ; moieties ; nucleobases ; nucleosides ; organic chemistry ; oxidation
Language	English
Dates of publication	2019-1115
Size	p. 16055-16067.
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.9b02550
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Article ; Online: Identification of a C3'-nitrile nucleoside analogue inhibitor of pancreatic cancer cell line growth.

Labbé, Marc-Olivier / Collins, Laura / Lefebvre, Carole-Anne / Maharsy, Wael / Beauregard, Janie / Dostie, Starr / Prévost, Michel / Nemer, Mona / Guindon, Yvan

Bioorganic & medicinal chemistry letters

2020 Volume 30, Issue 6, Page(s) 126983

Abstract: A synthetic strategy to access a novel family of nucleoside analogues bearing a C3'-nitrile substituted all-carbon quaternary center is presented herein. These purine bearing scaffolds were tested in two pancreatic cancer cell lines harboring either wild- ...

Abstract	A synthetic strategy to access a novel family of nucleoside analogues bearing a C3'-nitrile substituted all-carbon quaternary center is presented herein. These purine bearing scaffolds were tested in two pancreatic cancer cell lines harboring either wild-type (BxPC3) or G12V KRAS (Capan2) mutations. A promising compound was shown to have significantly greater efficacy in the Capan2 cell line as compared to Gemcitabine, the clinical gold standard used to treat pancreatic cancer.
MeSH term(s)	Amides/chemistry ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Apoptosis/drug effects ; Benzylamines/chemistry ; Cell Proliferation/drug effects ; Deoxycytidine/analogs & derivatives ; Deoxycytidine/chemistry ; Deoxycytidine/pharmacology ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Glycosylation ; Humans ; Mutation ; Nitriles/chemistry ; Pancreatic Neoplasms/drug therapy ; Phosphoric Acids/chemistry ; Proto-Oncogene Proteins p21(ras)/genetics ; Purines/chemistry ; Structure-Activity Relationship
Chemical Substances	Amides ; Antineoplastic Agents ; Benzylamines ; KRAS protein, human ; Nitriles ; Phosphoric Acids ; Purines ; Deoxycytidine (0W860991D6) ; phosphoramidic acid (9Q189608GB) ; benzylamine (A1O31ROR09) ; gemcitabine (B76N6SBZ8R) ; Proto-Oncogene Proteins p21(ras) (EC 3.6.5.2) ; purine (W60KTZ3IZY)
Language	English
Publishing date	2020-01-21
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2020.126983
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Article ; Online: Study of the endocyclic versus exocyclic C-O bond cleavage pathways of α- and β-methyl furanosides.

St-Jean, Olivier / Prévost, Michel / Guindon, Yvan

The Journal of organic chemistry

2013 Volume 78, Issue 7, Page(s) 2935–2946

Abstract: The activation and ring-opening of methyl furanosides in the four natural sugar scaffolds (ribo, lyxo, arabino, and xylo) efficiently afforded acyclic thioacetals with high S(N)2-like selectivity at the acetal center in the presence of Me2BBr and ... ...

Abstract	The activation and ring-opening of methyl furanosides in the four natural sugar scaffolds (ribo, lyxo, arabino, and xylo) efficiently afforded acyclic thioacetals with high S(N)2-like selectivity at the acetal center in the presence of Me2BBr and thiophenol. The stereochemical outcome of these reactions provides important mechanistic insights into the activation pathway of five-membered semicyclic acetals. The thioacetal products should find applications in oligosaccharides synthesis and allow further development of acyclic strategies for the synthesis of novel nucleoside analogues.
MeSH term(s)	Acetals/chemical synthesis ; Acetals/chemistry ; Fructose/analogs & derivatives ; Fructose/chemistry ; Molecular Structure ; Sulfhydryl Compounds/chemical synthesis ; Sulfhydryl Compounds/chemistry
Chemical Substances	Acetals ; Sulfhydryl Compounds ; Fructose (30237-26-4)
Language	English
Publishing date	2013-04-05
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/jo3027438
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