Stereoselective Synthesis of β-d-Manno-heptopyranoside Via CsCO-Mediated Anomeric -Alkylation: Synthesis of a Tetrasaccharide Repeat Unit of Surface-Layer Glycoprotein

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2022 May 10

PMID 35537215

Authors

Shuai Meng

Ishani Lakshika Hettiarachchi

Bishwa Raj Bhetuwal

Prakash Thapa

Jianglong Zhu

Affiliations

Soon will be listed here.

Abstract

Stereoselective synthesis of d-glycero- and l-glycero-β-d-mannoheptosides has been achieved by cesium carbonate-mediated β-selective anomeric -alkylation of the corresponding d-mannoheptoses. In addition, this method has been utilized in the total synthesis of a tetrasaccharide repeat unit of surface-layer glycoprotein.

Citing Articles

Synthesis of Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl -1,1-Dimethylpropargyl Carbamate Donors.

Gurung P, Shine G, Zhu J J Org Chem. 2024; 89(17):12547-12558.

PMID: 39137335 PMC: 11384238. DOI: 10.1021/acs.joc.4c01484.

Potassium carbonate-mediated -selective anomeric -alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids.

Lakshika Hettiarachchi I, Wu F, Stoica M, Li X, Zhu J Tetrahedron Lett. 2023; 122.

PMID: 37334260 PMC: 10270675. DOI: 10.1016/j.tetlet.2023.154511.

Synthesis of 2-Amino-2-deoxy-β-d-mannosides via Stereoselective Anomeric -Alkylation of 2,3-Oxazolidinone-Protected d-Mannosamine: Synthesis of the Trisaccharide Repeating Unit of 19F Polysaccharide.

Bhetuwal B, Wu F, Acharya P, Thapa P, Zhu J Org Lett. 2023; 25(22):4214-4218.

PMID: 37257021 PMC: 10330879. DOI: 10.1021/acs.orglett.3c01564.

References

Mulani S, Cheng K, Mong K . General Homologation Strategy for Synthesis of L-glycero- and D-glycero-Heptopyranoses. Org Lett. 2015; 17(22):5536-9. DOI: 10.1021/acs.orglett.5b02620. View

Meng S, Bhetuwal B, Acharya P, Zhu J . Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides. J Carbohydr Chem. 2019; 38(2):109-126. PMC: 6686909. DOI: 10.1080/07328303.2019.1581889. View

Crich D, Hu T, Cai F . Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates. J Org Chem. 2008; 73(22):8942-53. PMC: 2669227. DOI: 10.1021/jo801630m. View

Stanetty C, Baxendale I . Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa--acetyl-l-α-d--heptopyranose. European J Org Chem. 2015; 2015(12):2718-2726. PMC: 4464551. DOI: 10.1002/ejoc.201500024. View

Inuki S, Aiba T, Kawakami S, Akiyama T, Inoue J, Fujimoto Y . Chemical Synthesis of d-glycero-d-manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation. Org Lett. 2017; 19(12):3079-3082. DOI: 10.1021/acs.orglett.7b01158. View

Dohi H, Perion R, Durka M, Bosco M, Roue Y, Moreau F . Stereoselective glycal fluorophosphorylation: synthesis of ADP-2-fluoroheptose, an inhibitor of the LPS biosynthesis. Chemistry. 2008; 14(31):9530-9. DOI: 10.1002/chem.200801279. View

Meng S, Bhetuwal B, Nguyen H, Qi X, Fang C, Saybolt K . -Mannosylation via -Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans. European J Org Chem. 2020; 2020(15):2291-2301. PMC: 7236807. DOI: 10.1002/ejoc.202000313. View

Crich D, Banerjee A . Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl-.... J Am Chem Soc. 2006; 128(24):8078-86. PMC: 2617734. DOI: 10.1021/ja061594u. View

Tanaka M, Nakagawa A, Nishi N, Iijima K, Sawa R, Takahashi D . Boronic-Acid-Catalyzed Regioselective and 1,2- cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via Si-Type Mechanism. J Am Chem Soc. 2018; 140(10):3644-3651. DOI: 10.1021/jacs.7b12108. View

10.

Li T, Wang J, Zhu X, Zhou X, Sun S, Wang P . Synthesis of Rare 6-Deoxy-d-/l-Heptopyranosyl Fluorides: Assembly of a Hexasaccharide Corresponding to Strain CG8486 Capsular Polysaccharide. J Am Chem Soc. 2021; 143(29):11171-11179. DOI: 10.1021/jacs.1c05048. View

11.

Bhetuwal B, Wu F, Meng S, Zhu J . Stereoselective Synthesis of 2-Azido-2-deoxy-β-d-mannosides via CsCO-Mediated Anomeric O-Alkylation with Primary Triflates: Synthesis of a Tetrasaccharide Fragment of Teichuronic Acid. J Org Chem. 2020; 85(24):16196-16206. PMC: 7799176. DOI: 10.1021/acs.joc.0c02370. View

12.

Czaja J, Jachymek W, Niedziela T, Lugowski C, Aldova E, Kenne L . Structural studies of the O-specific polysaccharide from Plesiomonas shigelloides strain CNCTC 113/92. Eur J Biochem. 2000; 267(6):1672-9. DOI: 10.1046/j.1432-1327.2000.01161.x. View

13.

Ishiwata A, Lee Y, Ito Y . Recent advances in stereoselective glycosylation through intramolecular aglycon delivery. Org Biomol Chem. 2010; 8(16):3596-608. DOI: 10.1039/c004281a. View

14.

Zamyatina A, Gronow S, Puchberger M, Graziani A, Hofinger A, Kosma P . Efficient chemical synthesis of both anomers of ADP L-glycero- and D-glycero-D-manno-heptopyranose. Carbohydr Res. 2003; 338(23):2571-89. DOI: 10.1016/s0008-6215(03)00319-7. View

15.

Boltje T, Buskas T, Boons G . Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nat Chem. 2010; 1(8):611-22. PMC: 2794050. DOI: 10.1038/nchem.399. View

16.

Lakshika Hettiarachchi I, Meng S, Chahine M, Li X, Zhu J . Stereoselective β-Mannosylation via Anomeric -Alkylation with L-Sugar-Derived Electrophiles. European J Org Chem. 2022; 2021(48):6682-6687. PMC: 9389860. DOI: 10.1002/ejoc.202100903. View

17.

Niedziela T, Lukasiewicz J, Jachymek W, Dzieciatkowska M, Lugowski C, Kenne L . Core oligosaccharides of Plesiomonas shigelloides O54:H2 (strain CNCTC 113/92): structural and serological analysis of the lipopolysaccharide core region, the O-antigen biological repeating unit, and the linkage between them. J Biol Chem. 2002; 277(14):11653-63. DOI: 10.1074/jbc.M111885200. View

18.

Mettu R, Chen C, Wu C . Synthetic carbohydrate-based vaccines: challenges and opportunities. J Biomed Sci. 2020; 27(1):9. PMC: 6941340. DOI: 10.1186/s12929-019-0591-0. View

19.

Izumi S, Kobayashi Y, Takemoto Y . Regio- and Stereoselective Synthesis of 1,2- cis-Glycosides by Anomeric O-Alkylation with Organoboron Catalysis. Org Lett. 2019; 21(3):665-670. DOI: 10.1021/acs.orglett.8b03823. View

20.

Guerry P, Poly F, Riddle M, Maue A, Chen Y, Monteiro M . Campylobacter polysaccharide capsules: virulence and vaccines. Front Cell Infect Microbiol. 2012; 2:7. PMC: 3417588. DOI: 10.3389/fcimb.2012.00007. View