Expedient Azide-Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO4 with Cu(0) in Aqueous Media

doi:10.1021/acsorginorgau.3c00059

. 2023 Dec 19;4(2):235-240.

doi: 10.1021/acsorginorgau.3c00059. eCollection 2024 Apr 3.

Expedient Azide-Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO₄ with Cu(0) in Aqueous Media

Wen-Chieh Yang¹, Chien-Tien Chen¹

Affiliations

PMID: 38585512
PMCID: PMC10995936
DOI: 10.1021/acsorginorgau.3c00059

Expedient Azide-Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO₄ with Cu(0) in Aqueous Media

Wen-Chieh Yang et al. ACS Org Inorg Au. 2023.

. 2023 Dec 19;4(2):235-240.

doi: 10.1021/acsorginorgau.3c00059. eCollection 2024 Apr 3.

Authors

Wen-Chieh Yang¹, Chien-Tien Chen¹

Affiliation

¹ Department of Chemistry, National Tsing Hua University, No. 101, Section 2, Kuang-Fu Road, Hsinchu 30013, Taiwan R.O.C.

PMID: 38585512
PMCID: PMC10995936
DOI: 10.1021/acsorginorgau.3c00059

Abstract

A series of vanadium(III), vanadyl(IV/V) species, inorganic metal oxides, and transition-metal oxides was examined as cocatalysts with Cu(0) powder for copper(I)-catalyzed azide-alkyne cycloaddition. Among them, vanadyl(IV) species bearing acetylacetonate, acetate, and sulfate, vanadyl(V) isopropoxide, and vanadate were suitable for the click reactions of per-acetyl and per-benzyl β-azido glycosides with three different terminal alkynes in CH₃CN. Water-soluble vanadyl(IV) sulfate was further selected for efficient click reactions for unprotected β-glycosyl azides and even compatible with a thiol-containing substrate in aqueous media at ambient temperature.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

**Figure 1**
Monitored reaction progress.

**Scheme 1. Proposed Half-Reactions for Oxidation and Reduction in the Presence of Different Vanadyl(IV/V) Species and Copper Powder**

See this image and copyright information in PMC

References

1. Vala D. P.; Vala R. M.; Patel H. M. Versatile Synthetic Platform for 1,2,3-Triazole Chemistry. ACS Omega 2022, 7, 36945–36987. 10.1021/acsomega.2c04883. - DOI - PMC - PubMed
1. Thirumurugan P.; Matosiuk D.; Jozwiak K. Click chemistry for drug development and diverse chemical-biology applications. Chem. Rev. 2013, 113, 4905–4979. 10.1021/cr200409f. - DOI - PubMed
2. Tian G.; Song Q.; Liu Z.; Guo J.; Cao S.; Long S. Recent advances in 1,2,3- and 1,2,4-triazole hybrids as antimicrobials and their SAR: A critical review. Eur. J. Med. Chem. 2023, 259, 11560310.1016/j.ejmech.2023.115603. - DOI - PubMed
3. Sahu A.; Sahu P.; Agrawal R. A recent review on drug modification using 1, 2, 3-triazole. Curr. Chem. Biol. 2020, 14, 71–87. 10.2174/2212796814999200807214519. - DOI
4. Kolb H. C.; Sharpless K. B. The growing impact of click chemistry on drug discovery. Drug Disc. Today 2003, 8, 1128–1137. 10.1016/S1359-6446(03)02933-7. - DOI - PubMed
5. Chen C.-T.; Salunke S.; Wei T.-T.; Tang Y.-A.; Wang Y.-C. Fluorescent Nanohybrids from ZnS/CdSe Quantum Dots Functionalized with Triantennary, N-Hydroxy-p-(4-arylbutan-amido)benzamide/Gallamide Dendrons That Act as Inhibitors of Histone Deacetylase for Lung Cancer. ACS Appl. Bio Mater. 2021, 4, 2475–2489. 10.1021/acsabm.0c01438. - DOI - PubMed
1. Yang J.; Hoffmeister D.; Liu L.; Fu X.; Thorson J. S. Natural product glycorandomization. Bioorg. Med. Chem. Lett. 2004, 12, 1577–1584. 10.1016/j.bmc.2003.12.046. - DOI - PubMed
2. Zi C.-T.; Yang L.; Gao W.; Li Y.; Zhou J.; Ding Z.-T.; Hu J.; Jiang Z.-H. Click Glycosylation for the Synthesis of 1, 2, 3-Triazole-Linked Picropodophyllo-toxin Glycoconjugates and Their Anticancer Activity. ChemistrySelect 2017, 2, 5038–5044. 10.1002/slct.201700347. - DOI
1. For saccharides with click linkers:
2. Tiwari V. K.; Mishra B. B.; Mishra K. B.; Mishra N.; Singh A. S.; Chen X. Cu-Catalyzed Click Reaction in Carbohydrate Chemistry. Chem. Rev. 2016, 116, 3086–3240. 10.1021/acs.chemrev.5b00408. - DOI - PubMed
3. Bera S.; Linhardt R. J. Design and synthesis of unnatural heparosan and chondroitin building blocks. J. Org. Chem. 2011, 76, 3181–3193. 10.1021/jo200076z. - DOI - PMC - PubMed
4. Berthelot N.; Brossay A.; Gasciolli V.; Bono J.-J.; Baron A.; Beau J.-M.; Urban D.; Boyer F.-D.; Vauzeilles B. Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs. Org. Biomol. Chem. 2017, 15, 7802–7812. 10.1039/C7OB01201B. - DOI - PubMed
5. Cagnoni A. J.; Varela O.; Gouin S. G.; Kovensky J.; Uhrig M. L. Synthesis of Multivalent Glycoclusters from 1-Thio-β-d-galactose and Their Inhibitory Activity against the β-Galactosidase from E. coli. J. Org. Chem. 2011, 76, 3064–3077. 10.1021/jo102421e. - DOI - PubMed
6. Lee D. J.; Yang S.-H.; Williams G. M.; Brimble M. A. Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry. J. Org. Chem. 2012, 77, 7564–7571. 10.1021/jo3013435. - DOI - PubMed
7. Agrahari A. K.; Bose P.; Jaiswal M. K.; Rajkhowa S.; Singh A. S.; Hotha S.; Mishra N.; Tiwari V. K. Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications. Chem. Rev. 2021, 121, 7638–7956. 10.1021/acs.chemrev.0c00920. - DOI - PubMed
8. Bernardi A.; Sattin S. Interfering with the Sugar Code: Ten Years Later. Eur. J. Org. Chem. 2020, 2020, 4652–4663. 10.1002/ejoc.202000155. - DOI
1. Palomo C.; Aizpurua J. M.; Balentová E.; Azcune I.; Santos J. I.; Jiménez-Barbero J.; Cañada J.; Miranda J. I. Click” saccharide/β-lactam hybrids for lectin inhibition. Org. Lett. 2008, 10, 2227–2230. 10.1021/ol8006259. - DOI - PubMed
2. Sawa M.; Hsu T.-L.; Itoh T.; Sugiyama M.; Hanson S. R.; Vogt P. K.; Wong C.-H. Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12371–12376. 10.1073/pnas.0605418103. - DOI - PMC - PubMed
3. Alcaide B.; Almendros P.; Aragoncillo C.; Callejo R.; Ruiz M. P.; Torres M. R. Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence. J. Org. Chem. 2012, 77, 6917–6928. 10.1021/jo301113g. - DOI - PubMed
4. la Venia A.; Kovalová A.; Vrabel M.. CuAAC in Protein Conjugation. In Click Chemistry ,1st ed.; Rutjes F. P. J. T., Ed.; Science of Synthesis series; Georg Thieme Verlag KG: Stuggart, Germany, 2022; Vol. 2021/4, pp 95–134.

LinkOut - more resources

Full Text Sources
- PubMed Central

[1] Vala D. P.; Vala R. M.; Patel H. M. Versatile Synthetic Platform for 1,2,3-Triazole Chemistry. ACS Omega 2022, 7, 36945–36987. 10.1021/acsomega.2c04883. - DOI - PMC - PubMed

[2] Vala D. P.; Vala R. M.; Patel H. M. Versatile Synthetic Platform for 1,2,3-Triazole Chemistry. ACS Omega 2022, 7, 36945–36987. 10.1021/acsomega.2c04883. - DOI - PMC - PubMed

[3] Thirumurugan P.; Matosiuk D.; Jozwiak K. Click chemistry for drug development and diverse chemical-biology applications. Chem. Rev. 2013, 113, 4905–4979. 10.1021/cr200409f. - DOI - PubMed

Tian G.; Song Q.; Liu Z.; Guo J.; Cao S.; Long S. Recent advances in 1,2,3- and 1,2,4-triazole hybrids as antimicrobials and their SAR: A critical review. Eur. J. Med. Chem. 2023, 259, 11560310.1016/j.ejmech.2023.115603. - DOI - PubMed

Sahu A.; Sahu P.; Agrawal R. A recent review on drug modification using 1, 2, 3-triazole. Curr. Chem. Biol. 2020, 14, 71–87. 10.2174/2212796814999200807214519. - DOI

Kolb H. C.; Sharpless K. B. The growing impact of click chemistry on drug discovery. Drug Disc. Today 2003, 8, 1128–1137. 10.1016/S1359-6446(03)02933-7. - DOI - PubMed

Chen C.-T.; Salunke S.; Wei T.-T.; Tang Y.-A.; Wang Y.-C. Fluorescent Nanohybrids from ZnS/CdSe Quantum Dots Functionalized with Triantennary, N-Hydroxy-p-(4-arylbutan-amido)benzamide/Gallamide Dendrons That Act as Inhibitors of Histone Deacetylase for Lung Cancer. ACS Appl. Bio Mater. 2021, 4, 2475–2489. 10.1021/acsabm.0c01438. - DOI - PubMed

[4] Thirumurugan P.; Matosiuk D.; Jozwiak K. Click chemistry for drug development and diverse chemical-biology applications. Chem. Rev. 2013, 113, 4905–4979. 10.1021/cr200409f. - DOI - PubMed

[5] Tian G.; Song Q.; Liu Z.; Guo J.; Cao S.; Long S. Recent advances in 1,2,3- and 1,2,4-triazole hybrids as antimicrobials and their SAR: A critical review. Eur. J. Med. Chem. 2023, 259, 11560310.1016/j.ejmech.2023.115603. - DOI - PubMed

[6] Sahu A.; Sahu P.; Agrawal R. A recent review on drug modification using 1, 2, 3-triazole. Curr. Chem. Biol. 2020, 14, 71–87. 10.2174/2212796814999200807214519. - DOI

[7] Kolb H. C.; Sharpless K. B. The growing impact of click chemistry on drug discovery. Drug Disc. Today 2003, 8, 1128–1137. 10.1016/S1359-6446(03)02933-7. - DOI - PubMed

[8] Chen C.-T.; Salunke S.; Wei T.-T.; Tang Y.-A.; Wang Y.-C. Fluorescent Nanohybrids from ZnS/CdSe Quantum Dots Functionalized with Triantennary, N-Hydroxy-p-(4-arylbutan-amido)benzamide/Gallamide Dendrons That Act as Inhibitors of Histone Deacetylase for Lung Cancer. ACS Appl. Bio Mater. 2021, 4, 2475–2489. 10.1021/acsabm.0c01438. - DOI - PubMed

[9] Yang J.; Hoffmeister D.; Liu L.; Fu X.; Thorson J. S. Natural product glycorandomization. Bioorg. Med. Chem. Lett. 2004, 12, 1577–1584. 10.1016/j.bmc.2003.12.046. - DOI - PubMed

Zi C.-T.; Yang L.; Gao W.; Li Y.; Zhou J.; Ding Z.-T.; Hu J.; Jiang Z.-H. Click Glycosylation for the Synthesis of 1, 2, 3-Triazole-Linked Picropodophyllo-toxin Glycoconjugates and Their Anticancer Activity. ChemistrySelect 2017, 2, 5038–5044. 10.1002/slct.201700347. - DOI

[10] Yang J.; Hoffmeister D.; Liu L.; Fu X.; Thorson J. S. Natural product glycorandomization. Bioorg. Med. Chem. Lett. 2004, 12, 1577–1584. 10.1016/j.bmc.2003.12.046. - DOI - PubMed

[11] Zi C.-T.; Yang L.; Gao W.; Li Y.; Zhou J.; Ding Z.-T.; Hu J.; Jiang Z.-H. Click Glycosylation for the Synthesis of 1, 2, 3-Triazole-Linked Picropodophyllo-toxin Glycoconjugates and Their Anticancer Activity. ChemistrySelect 2017, 2, 5038–5044. 10.1002/slct.201700347. - DOI

[12] For saccharides with click linkers:

Tiwari V. K.; Mishra B. B.; Mishra K. B.; Mishra N.; Singh A. S.; Chen X. Cu-Catalyzed Click Reaction in Carbohydrate Chemistry. Chem. Rev. 2016, 116, 3086–3240. 10.1021/acs.chemrev.5b00408. - DOI - PubMed

Bera S.; Linhardt R. J. Design and synthesis of unnatural heparosan and chondroitin building blocks. J. Org. Chem. 2011, 76, 3181–3193. 10.1021/jo200076z. - DOI - PMC - PubMed

Berthelot N.; Brossay A.; Gasciolli V.; Bono J.-J.; Baron A.; Beau J.-M.; Urban D.; Boyer F.-D.; Vauzeilles B. Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs. Org. Biomol. Chem. 2017, 15, 7802–7812. 10.1039/C7OB01201B. - DOI - PubMed

Cagnoni A. J.; Varela O.; Gouin S. G.; Kovensky J.; Uhrig M. L. Synthesis of Multivalent Glycoclusters from 1-Thio-β-d-galactose and Their Inhibitory Activity against the β-Galactosidase from E. coli. J. Org. Chem. 2011, 76, 3064–3077. 10.1021/jo102421e. - DOI - PubMed

Lee D. J.; Yang S.-H.; Williams G. M.; Brimble M. A. Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry. J. Org. Chem. 2012, 77, 7564–7571. 10.1021/jo3013435. - DOI - PubMed

Agrahari A. K.; Bose P.; Jaiswal M. K.; Rajkhowa S.; Singh A. S.; Hotha S.; Mishra N.; Tiwari V. K. Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications. Chem. Rev. 2021, 121, 7638–7956. 10.1021/acs.chemrev.0c00920. - DOI - PubMed

Bernardi A.; Sattin S. Interfering with the Sugar Code: Ten Years Later. Eur. J. Org. Chem. 2020, 2020, 4652–4663. 10.1002/ejoc.202000155. - DOI

[13] For saccharides with click linkers:

[14] Tiwari V. K.; Mishra B. B.; Mishra K. B.; Mishra N.; Singh A. S.; Chen X. Cu-Catalyzed Click Reaction in Carbohydrate Chemistry. Chem. Rev. 2016, 116, 3086–3240. 10.1021/acs.chemrev.5b00408. - DOI - PubMed

[15] Bera S.; Linhardt R. J. Design and synthesis of unnatural heparosan and chondroitin building blocks. J. Org. Chem. 2011, 76, 3181–3193. 10.1021/jo200076z. - DOI - PMC - PubMed

[16] Berthelot N.; Brossay A.; Gasciolli V.; Bono J.-J.; Baron A.; Beau J.-M.; Urban D.; Boyer F.-D.; Vauzeilles B. Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs. Org. Biomol. Chem. 2017, 15, 7802–7812. 10.1039/C7OB01201B. - DOI - PubMed

[17] Cagnoni A. J.; Varela O.; Gouin S. G.; Kovensky J.; Uhrig M. L. Synthesis of Multivalent Glycoclusters from 1-Thio-β-d-galactose and Their Inhibitory Activity against the β-Galactosidase from E. coli. J. Org. Chem. 2011, 76, 3064–3077. 10.1021/jo102421e. - DOI - PubMed

[18] Lee D. J.; Yang S.-H.; Williams G. M.; Brimble M. A. Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry. J. Org. Chem. 2012, 77, 7564–7571. 10.1021/jo3013435. - DOI - PubMed

[19] Agrahari A. K.; Bose P.; Jaiswal M. K.; Rajkhowa S.; Singh A. S.; Hotha S.; Mishra N.; Tiwari V. K. Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications. Chem. Rev. 2021, 121, 7638–7956. 10.1021/acs.chemrev.0c00920. - DOI - PubMed

[20] Bernardi A.; Sattin S. Interfering with the Sugar Code: Ten Years Later. Eur. J. Org. Chem. 2020, 2020, 4652–4663. 10.1002/ejoc.202000155. - DOI

[21] Palomo C.; Aizpurua J. M.; Balentová E.; Azcune I.; Santos J. I.; Jiménez-Barbero J.; Cañada J.; Miranda J. I. Click” saccharide/β-lactam hybrids for lectin inhibition. Org. Lett. 2008, 10, 2227–2230. 10.1021/ol8006259. - DOI - PubMed

Sawa M.; Hsu T.-L.; Itoh T.; Sugiyama M.; Hanson S. R.; Vogt P. K.; Wong C.-H. Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12371–12376. 10.1073/pnas.0605418103. - DOI - PMC - PubMed

Alcaide B.; Almendros P.; Aragoncillo C.; Callejo R.; Ruiz M. P.; Torres M. R. Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence. J. Org. Chem. 2012, 77, 6917–6928. 10.1021/jo301113g. - DOI - PubMed

la Venia A.; Kovalová A.; Vrabel M.. CuAAC in Protein Conjugation. In Click Chemistry ,1st ed.; Rutjes F. P. J. T., Ed.; Science of Synthesis series; Georg Thieme Verlag KG: Stuggart, Germany, 2022; Vol. 2021/4, pp 95–134.

[22] Palomo C.; Aizpurua J. M.; Balentová E.; Azcune I.; Santos J. I.; Jiménez-Barbero J.; Cañada J.; Miranda J. I. Click” saccharide/β-lactam hybrids for lectin inhibition. Org. Lett. 2008, 10, 2227–2230. 10.1021/ol8006259. - DOI - PubMed

[23] Sawa M.; Hsu T.-L.; Itoh T.; Sugiyama M.; Hanson S. R.; Vogt P. K.; Wong C.-H. Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12371–12376. 10.1073/pnas.0605418103. - DOI - PMC - PubMed

[24] Alcaide B.; Almendros P.; Aragoncillo C.; Callejo R.; Ruiz M. P.; Torres M. R. Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence. J. Org. Chem. 2012, 77, 6917–6928. 10.1021/jo301113g. - DOI - PubMed

[25] la Venia A.; Kovalová A.; Vrabel M.. CuAAC in Protein Conjugation. In Click Chemistry ,1st ed.; Rutjes F. P. J. T., Ed.; Science of Synthesis series; Georg Thieme Verlag KG: Stuggart, Germany, 2022; Vol. 2021/4, pp 95–134.

Save citation to file

Email citation

Add to Collections

Add to My Bibliography

Your saved search

Create a file for external citation management software

Your RSS Feed

Expedient Azide-Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO₄ with Cu(0) in Aqueous Media

Affiliation

Expedient Azide-Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO₄ with Cu(0) in Aqueous Media

Authors

Affiliation

Abstract

Conflict of interest statement

Figures

Similar articles

References

LinkOut - more resources

Full Text Sources