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Recent Advances Related to Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry

João Rufino de Freitas Filho, Jucleiton José Rufino de Freitas, Pedro Ramos de Souza Neto, Fabrícia Aparecida Marques de Souza, Adiel Soares Ferreira, Anne Gabrielle Marques da Silva, Francisco Antonio Mabson Henrique Lopes, Marcílio Martins de Moraes, Clécio Souza Ramos, Ronaldo Nascimentos de Oliveira

International Research Journal of Pure and Applied Chemistry · pp. 95–110 · Published 22 Sep 2023

10.9734/irjpac/2023/v24i5830

Abstract

The anomeric effect in carbohydrate chemistry is known as the interaction between the OHd substituent at the anomeric position to favor an axial orientation rather than an equatorial one, despite the increased 1,3-diaxial interactions. In the anomeric effect, a sugar ring is stabilized by an electronegative substituent at the C1 carbon, also known as the anomeric carbon. The stabilization is thought to result from interactions between lone electron pairs on oxygen and a C1 antibonding orbital. On the other hand, the anomeric effect can be of two types: endo-anomeric and exo-anomeric. The effect is called endo-anomeric when the lone pair comes from the oxygen atom in the sugar ring and exo-anomeric when the lone pair comes from oxygen in a substituent on C1. Several factors influence the anomeric effect. In this way, this review aims to describe the recent advances in main theories, observations, and advances achieved in the last decades related to the anomeric effect. GRAPHICAL ABSTRACT

Carbohydrate chemistry glycoside anomeric effect exo-anomeric

References (77)

  1. 1 The relative affinities of ligand atoms for acceptor molecules and ions [DOI]
  2. 2 Application of the Principle of Hard and Soft Acids and Bases to Organic Chemistry [DOI]
  3. 3 Ethanolic Extract of Propolis (EEP) Enhances the Apoptosis- Inducing Potential of TRAIL in Cancer Cells [DOI]
  4. 4 Hard soft acids bases (HSAB) principle and organic chemistry [DOI]
  5. 5 Recent studies of the anomeric effect [DOI]
  6. 6 Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry [DOI]
  7. 7 Handbook of Chemical Glycosylation [DOI]
  8. 8 Methods for 2-Deoxyglycoside Synthesis [DOI]
  9. 9 The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface [DOI]
  10. 10 Chemical O‐Glycosylations: An Overview [DOI]
  11. 11 Recent Developments in the Ferrier Rearrangement [DOI]
  12. 12 Mechanisms of Glycosylation Reactions Studied by Low-Temperature Nuclear Magnetic Resonance [DOI]
  13. 13 Glycosyl Cross-Coupling of Anomeric Nucleophiles: Scope, Mechanism, and Applications in the Synthesis of Aryl C -Glycosides [DOI]
  14. 14 Sensing the anomeric effect in a solvent-free environment [DOI]
  15. 15 Design of α-Selective Glycopyranosyl Donors Relying on Remote Anchimeric Assistance [DOI]
  16. 16 Origin and Nature of Bond Rotation Barriers: A Unified View [DOI]
  17. 17 Recent Advances in Organocatalytic Glycosylations [DOI]
  18. 18 Influence of solvent on the magnitude of the anomeric effect [DOI]
  19. 19 Double Stereodifferentiation in Carbohydrate Coupling Reactions: The Mismatched Interaction of Donor and Acceptor as an Unprecedented Factor Governing the α/β Ratio of Glycoside Formation [DOI]
  20. 20 The Anomeric Effect: It’s Complicated [DOI]
  21. 21 The anomeric effect on the basis of natural bond orbital analysis [DOI]
  22. 22 Synergistic solvent effect in 1,2-cis-glycoside formation [DOI]
  23. 23 Controlling the stereoselectivity of glycosylation via solvent effects [DOI]
  24. 24 The anomeric effect: the dominance of exchange effects in closed-shell systems [DOI]
  25. 25 How Solvent Influences the Anomeric Effect: Roles of Hyperconjugative versus Steric Interactions on the Conformational Preference [DOI]
  26. 26 Strategies toward protecting group-free glycosylation through selective activation of the anomeric center [DOI]
  27. 27 The Problem of Origins and Origins of the Problem: Influence of Language on Studies Concerning the Anomeric Effect [DOI]
  28. 28 Is there a generalized anomeric effect? Analyses from energy components and information-theoretic quantities from density functional reactivity theory [DOI]
  29. 29 Oxidative Activation of C–S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides [DOI]
  30. 30 How the Generalized Anomeric Effect Influences the Conformational Preference [DOI]
  31. 31 Rhamnosylation: Diastereoselectivity of Conformationally Armed Donors [DOI]
  32. 32 Recent progress in the field of glycoconjugates [DOI]
  33. 33 Theoretical study on the anomeric effect in α-substituted tetrahydropyrans and piperidines [DOI]
  34. 34 Anomeric O-Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs [DOI]
  35. 35 Hyperconjugative interactions are the main responsible for the anomeric effect: a direct relationship between the hyperconjugative anomeric effect, global hardness and zero-point energy [DOI]
  36. 36 Experimental studies of the anomeric effect [DOI]
  37. 37 Kinetics of oxygen exchange at the anomeric carbon atom of D-glucose and D-erythrose using the oxygen-18 isotope effect in carbon-13 nuclear magnetic resonance spectroscopy [DOI]
  38. 38 Hyperconjugation Effect in Substituted Methyl Boranes: An Orbital Deletion Procedure Analysis [DOI]
  39. 39 Anomeric effect revisited: Perspective from information-theoretic approach in density functional reactivity theory [DOI]
  40. 40 Stereoelectronic Effects: Analysis by Computational and Theoretical Methods [DOI]
  41. 41 Synthesis of 2,3-Unsaturated Alkynyl O-Glucosides from Tri-O-acetyl-d-glucal by Using Montmorillonite K-10/Iron(III) Chloride Hexahydrate with Subsequent Copper(I)-Catalyzed 1,3-Dipolar Cycloaddition [DOI]
  42. 42 Conformational studies of gas-phase ribose and 2-deoxyribose by density functional, second order PT and multi-level method calculations: the pyranoses, furanoses, and open-chain structures [DOI]
  43. 43 The formation of carbon–carbon and carbon–heteroatom bonds using silver tetrafluoroborate as a promoter [DOI]
  44. 44 Conformational behavior of peracetylated β-d-mannopyranosyl methanesulfonamide: implications for the mechanism of sulfonamidoglycosylation of carbohydrate derivatives [DOI]
  45. 45 Conformational analysis. XV. Conformational enthalpy, entropy, and free energy of the carboxyl, carboxylate, carbomethoxy, carbonyl chloride, and methyl ketone groups [DOI]
  46. 46 Glycosylation reaction under high pressure [DOI]
  47. 47 Effects of solvent and anomeric configuration upon the circular dichroism, temperature dependence of amide proton chemical shifts, amide proton exchange rates, and infrared absorption of methyl 2-acetamido-2-deoxy-D-glucopyranosides [DOI]
  48. 48 Influence of acetylation on anomeric effect in methyl glycosides [DOI]
  49. 49 Anomeric Effect in Carbohydrates: Facts and Hypothesis [DOI]
  50. 50 Using density functional theory to calculate the anomeric effect in hydroxylamine and hydrazide derivatives of tetrahydropyran [DOI]
  51. 51 A review on biomass: importance, chemistry, classification, and conversion [DOI]
  52. 52 Diastereoselective Synthesis of Aryl C‐Glycosides from Glycosyl Esters via C−O Bond Homolysis [DOI]
  53. 53 Anomeric effect, hyperconjugation and electrostatics: lessons from complexity in a classic stereoelectronic phenomenon [DOI]
  54. 54 Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone [DOI]
  55. 55 Hyperconjugation [DOI]
  56. 56 Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of α‐Glycans up to a 30‐mer [DOI]
  57. 57 Transition metal catalyzed glycosylation reactions – an overview [DOI]
  58. 58 Carbohydrates [DOI]
  59. 59 Stereoelectronic Effects Impact Glycan Recognition [DOI]
  60. 60 Are Brønsted Acids the True Promoter of Metal-Triflate-Catalyzed Glycosylations? A Mechanistic Probe into 1,2-cis-Aminoglycoside Formation by Nickel Triflate [DOI]
  61. 61 Catalytic synthesis of new pyrazolo [3,4-b] pyridine via a cooperative vinylogous anomeric-based oxidation [DOI]
  62. 62 Regio- and Stereoselective Synthesis of 1,2-cis-Glycosides by Anomeric O-Alkylation with Organoboron Catalysis [DOI]
  63. 63 Organocatalysis: A recent development on stereoselective synthesis of o-glycosides [DOI]
  64. 64 Anomeric Effect in Saturated Heterocyclic Ring Systems [DOI]
  65. 65 Reengineering Chemical Glycosylation: Direct, Metal‐Free Anomeric O‐Arylation of Unactivated Carbohydrates [DOI]
  66. 66 The endo‐ and exo‐Anomeric Effects in Furanosides. A Computational Study [DOI]
  67. 67 Fluorine‐Induced Pseudo‐Anomeric Effects in Methoxycyclohexanes through Electrostatic 1,3‐Diaxial Interactions [DOI]
  68. 68 Probing the anomeric effect and mechanism of isomerization of oxazinane rings by DFT methods [DOI]
  69. 69 Comparison of Conformational Analyses of Naturally Occurring Flavonoid-O-Glycosides with Unnatural Flavonoid-CF2-Glycosides Using Molecular Modeling [DOI]
  70. 70 Recent Advances in the Synthesis of Bioactive Glycohybrids via Click-Chemistry [DOI]
  71. 71 Contribution of Hyperconjugation and Inductive Effects to the Pseudo -anomeric Effect in 4-Substituted Methoxycyclohexanes [DOI]
  72. 72 One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides [DOI]
  73. 73 An Interacting Quantum Atoms (IQA) and Relative Energy Gradient (REG) Analysis of the Anomeric Effect [DOI]
  74. 74 Anomeric effect in pyranose-ring derivatives containing carbon, silicon, and germanium as anomeric centers: an ab initio systematic study [DOI]
  75. 75 Carbocyclic Substrate Analogues Reveal Kanosamine Biosynthesis Begins with the α-Anomer of Glucose 6-Phosphate [DOI]
  76. 76 DESENVOLVIMENTO NOS MÉTODOS DE GLICOSILAÇÃO: UMA CHAVE PARA ACESSAR SUAS APLICAÇÕES NA SÍNTESE DE MOLÉCULAS BIOATIVAS [DOI]
  77. 77 10.33224/rrch.2023.68.1-2 [DOI]

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