Gram Scale Production of 1-azido-β-d-glucose Enzyme Catalysis for the Synthesis of 1,2,3-triazole-glucosides

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 6

PMID 35517277

Authors

Jaggaiah N Gorantla

Salila Pengthaisong

Sunaree Choknud

Teadkait Kaewpuang

Tanaporn Manyum

Vinich Promarak

James R Ketudat Cairns

Affiliations

Soon will be listed here.

Abstract

The production of analytical amounts of azido sugars is used as a means of verifying catalytic acid/base mutations of retaining glycosidase, but application of this process to preparative synthesis has not been reported. The catalytic acid/base mutant of GH116 β-glucosidase, GH116D593A, catalyzed the gram scale production of 1-azido-β-d-glucose (1) from -nitropheyl-β-d-glucopyranoside (NPGlc) and azide a transglucosylation reaction. Overnight reaction of the enzyme with NPGlc and NaN in aqueous MES buffer (pH 5.5) at 55 °C produced 1 (3.27 g), which was isolated as a white foamy solid in 96% yield. This 1 was successfully utilized for the synthesis of fifteen 1,2,3-triazole-β-d-glucosyl derivatives (2-16) containing a variety of functional groups, click chemistry.

Citing Articles

Chemoenzymatic and Protecting-Group-Free Synthesis of 1,4-Substituted 1,2,3-Triazole-α-d-glucosides with Potent Inhibitory Activity toward Lysosomal α-Glucosidase.

Gorantla J, Maniganda S, Pengthaisong S, Ngiwsara L, Sawangareetrakul P, Chokchaisiri S ACS Omega. 2021; 6(39):25710-25719.

PMID: 34632227 PMC: 8495876. DOI: 10.1021/acsomega.1c03928.

References

Rossi L, Basu A . Glycosidase inhibition by 1-glycosyl-4-phenyl triazoles. Bioorg Med Chem Lett. 2005; 15(15):3596-9. DOI: 10.1016/j.bmcl.2005.05.081. View

Beniazza R, Bayo N, Molton F, Duboc C, Massip S, McClenaghan N . Effective ascorbate-free and photolatent click reactions in water using a photoreducible copper(II)-ethylenediamine precatalyst. Beilstein J Org Chem. 2015; 11:1950-9. PMC: 4661010. DOI: 10.3762/bjoc.11.211. View

Wang Q, Trimbur D, Graham R, Warren R, Withers S . Identification of the acid/base catalyst in Agrobacterium faecalis beta-glucosidase by kinetic analysis of mutants. Biochemistry. 1995; 34(44):14554-62. DOI: 10.1021/bi00044a034. View

Kim D, Choe Y, Jung K, Lee K, Choi J, Choi Y . A (18)F-labeled glucose analog: synthesis using a click labeling method and in vitro evaluation. Arch Pharm Res. 2008; 31(5):587-93. DOI: 10.1007/s12272-001-1197-2. View

Wombacher R, Keiper S, Suhm S, Serganov A, Patel D, Jaschke A . Control of stereoselectivity in an enzymatic reaction by backdoor access. Angew Chem Int Ed Engl. 2006; 45(15):2469-72. PMC: 4693636. DOI: 10.1002/anie.200503280. View

Lopez M, Bornaghi L, Innocenti A, Vullo D, Charman S, Supuran C . Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010; 53(7):2913-26. DOI: 10.1021/jm901888x. View

Tanaka T, Nagai H, Noguchi M, Kobayashi A, Shoda S . One-step conversion of unprotected sugars to beta-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution. Chem Commun (Camb). 2009; (23):3378-9. DOI: 10.1039/b905761g. View

Feast G, Hutt O, Mulet X, Conn C, Drummond C, Savage G . The high-throughput synthesis and phase characterisation of amphiphiles: a sweet case study. Chemistry. 2014; 20(10):2783-92. DOI: 10.1002/chem.201303514. View

Knowles J . Enzyme catalysis: not different, just better. Nature. 1991; 350(6314):121-4. DOI: 10.1038/350121a0. View

10.

Goyard D, Chajistamatiou A, Sotiropoulou A, Chrysina E, Praly J, Vidal S . Efficient atropodiastereoselective access to 5,5'-bis-1,2,3-triazoles: studies on 1-glucosylated 5-halogeno 1,2,3-triazoles and their 5-substituted derivatives as glycogen phosphorylase inhibitors. Chemistry. 2014; 20(18):5423-32. DOI: 10.1002/chem.201304989. View

11.

Carroux C, Rankin G, Moeker J, Bornaghi L, Katneni K, Morizzi J . A prodrug approach toward cancer-related carbonic anhydrase inhibition. J Med Chem. 2013; 56(23):9623-34. DOI: 10.1021/jm401163e. View

12.

Massarotti A, Aprile S, Mercalli V, Del Grosso E, Grosa G, Sorba G . Are 1,4- and 1,5-disubstituted 1,2,3-triazoles good pharmacophoric groups?. ChemMedChem. 2014; 9(11):2497-508. DOI: 10.1002/cmdc.201402233. View

13.

Yu G, Ma Y, Han C, Yao Y, Tang G, Mao Z . A sugar-functionalized amphiphilic pillar[5]arene: synthesis, self-assembly in water, and application in bacterial cell agglutination. J Am Chem Soc. 2013; 135(28):10310-3. DOI: 10.1021/ja405237q. View

14.

Beniazza R, Lambert R, Harmand L, Molton F, Duboc C, Denisov S . Sunlight-driven copper-catalyst activation applied to photolatent click chemistry. Chemistry. 2014; 20(41):13181-7. DOI: 10.1002/chem.201404056. View

15.

Anand N, Jaiswal N, Pandey S, Srivastava A, Tripathi R . Application of click chemistry towards an efficient synthesis of 1,2,3-1H-triazolyl glycohybrids as enzyme inhibitors. Carbohydr Res. 2010; 346(1):16-25. DOI: 10.1016/j.carres.2010.10.017. View

16.

Bokor E, Kyriakis E, Solovou T, Koppany C, Kantsadi A, Szabo K . Nanomolar Inhibitors of Glycogen Phosphorylase Based on β-d-Glucosaminyl Heterocycles: A Combined Synthetic, Enzyme Kinetic, and Protein Crystallography Study. J Med Chem. 2017; 60(22):9251-9262. DOI: 10.1021/acs.jmedchem.7b01056. View

17.

Goyard D, Docsa T, Gergely P, Praly J, Vidal S . Synthesis of 4-amidomethyl-1-glucosyl-1,2,3-triazoles and evaluation as glycogen phosphorylase inhibitors. Carbohydr Res. 2014; 402:245-51. DOI: 10.1016/j.carres.2014.10.009. View

18.

Delso I, Valero-Gonzalez J, Gomollon-Bel F, Castro-Lopez J, Fang W, Navratilova I . Inhibitors against Fungal Cell Wall Remodeling Enzymes. ChemMedChem. 2017; 13(2):128-132. DOI: 10.1002/cmdc.201700720. View

19.

Muthana S, Yu H, Cao H, Cheng J, Chen X . Chemoenzymatic synthesis of a new class of macrocyclic oligosaccharides. J Org Chem. 2009; 74(8):2928-36. DOI: 10.1021/jo8027856. View

20.

Charoenwattanasatien R, Pengthaisong S, Breen I, Mutoh R, Sansenya S, Hua Y . Bacterial β-Glucosidase Reveals the Structural and Functional Basis of Genetic Defects in Human Glucocerebrosidase 2 (GBA2). ACS Chem Biol. 2016; 11(7):1891-900. PMC: 4949581. DOI: 10.1021/acschembio.6b00192. View