Synthesis of a bicyclic analog of l-iduronic acid adopting the biologically relevant 2 S 0 conformation

Herrera, Antonio J.; Beneitez, M. Templo; Amorim, Luis; Cañada, F. Javier; Jiménez‐Barbero, Jesús; Sînaÿ, Pierre; Blériot, Yves

doi:10.1016/j.carres.2007.02.025

Cited by 10 publications

(4 citation statements)

References 41 publications

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“…Generally, pyranose sugars (6-membered ring system consisting of 5 ring carbons and 1 oxygen) such as iduronic acid are present in different conformations simultaneously: chair conformations ( 4 C 1 , 1 C 4 ) or skew-boat conformation ( 2 S O ) (Figure 2A). These conformations are in equilibrium to each other when sugars are in solution and the glycosidic bonds confer a small degree of freedom to switch between conformations [57]. In this context, the role of 2-O sulfation (IduA) for binding of antithrombin III AT-III for anti-coagulation purposes is important, as the 2-O-sulfation (IduA) as well as the 3-O-sulfation (GlcNS3.6S) instigate a conformational change to the skew-boat conformation upon binding of heparin to AT-III [58].…”

Section: Gag-protein Binding: a Function Of Sulfation Pattern 3d Cmentioning

confidence: 99%

“…Once bound to AT-III, heparin potentiates the anticoagulant activity of AT-III by factor 2000 [59]. However, the AT-III binding region [57, 58, 60, 61] lies outside of the active binding region for FGFs (FGF-1/2) [62], so the relative contribution of GAG conformation to interaction with FGF remains unknown. The carbohydrate conformations and sulfate group activities that are relevant for protein binding are summarized in Figure 3.…”

Section: Gag-protein Binding: a Function Of Sulfation Pattern 3d Cmentioning

confidence: 99%

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Molecular engineering of glycosaminoglycan chemistry for biomolecule delivery

Miller

Goude

McDevitt³

et al. 2014

Acta Biomaterialia

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Glycosaminoglycans (GAGs) are linear, negatively charged polysaccharid es that interact with a variety of positively-charged growth factors. In this review article, the effects of engineering GAG chemistry for molecular delivery applications in regenerative medicine are presented. Three major areas of focus at the structure-function-property interface are discussed: 1) macromolecular properties of GAGs, 2) effects of chemical modifications on protein binding, and 3) degradation mechanisms of GAGs. GAG-protein interactions can be based on 1) GAG sulfation pattern, 2) GAG carbohydrate conformation, and 3) GAG polyelectrolyte behavior. Chemical modifications of GAGs, which are commonly performed to engineer molecular delivery systems, affect protein binding and are highly dependent on the site of modification on the GAG molecules. The rate and mode of degradation can determine the release of molecules as well as the length of GAG fragments to which the cargo is electrostatically coupled and eventually released from the delivery system. Overall, GAG-based polymers are a versatile biomaterial platform offering novel means to engineer molecular delivery systems with a high degree of control in order to better treat a range of degenerate or injured tissues.

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Section: Gag-protein Binding: a Function Of Sulfation Pattern 3d Cmentioning

confidence: 99%

Section: Gag-protein Binding: a Function Of Sulfation Pattern 3d Cmentioning

confidence: 99%

Molecular engineering of glycosaminoglycan chemistry for biomolecule delivery

Miller

Goude

McDevitt³

et al. 2014

Acta Biomaterialia

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“…For our purpose, we used a similar synthetic strategy to the one used previously to determine the active conformation of L-iduronic acid in heparin by locking the sugar unit in a defined conformation through its chemical bridging. 52, 53 We designed and studied xylopyranoside analogues locked in the requisite 2,5 B boat conformation. To retain all the hydroxyl groups of the parent glycoside and force the pyranose ring to adopt a boat conformation, we selected a 2-oxabicyclo[2.…”

Section: The Xylopyranose Casementioning

confidence: 99%

Contributing to the Study of Enzymatic and Chemical Glycosyl Transfer Through the Observation and Mimicry of Glycosyl Cations

Blériot¹

2020

Synthesis

Self Cite

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This account describes our efforts dedicated to: 1) the design of glycomimetics aimed at targeting therapeutically relevant carbohydrate processing enzymes, and 2) the observation, characterization, and exploitation of glycosyl cations as a tool for studying the glycosylation reaction. These findings have brought important data regarding this key ionic species as well as innovative strategies to access iminosugars of interest.1 Introduction2 The Glycosyl Cation, A Central Species in Glycosciences2.1 A Selection of the Strategies Developed so far to Gain Insights into Glycosyl Cations Structure2.2 When Superacids Meet Carbohydrates3 Chemical Probes to Gain Insights into the Pseudorotational Itinerary of Glycosides During Glycosidic Bond Hydrolysis3.1 Conformationally Locked Glycosides3.1.1 The Xylopyranose Case3.1.2 The Mannopyranose Case3.2 Conformationally Flexible Iminosugars3.2.1 Nojirimycin Ring Homologues3.2.2 Noeuromycin Ring Homologues3.2.3 Seven-Membered Iminosugar C-Glycosides4 N-Acetyl-d-glucosamine Mimics5 Ring Contraction: A Useful Tool to Increase Iminosugar’s Structural Diversity6 Regioselective Deprotection of Iminosugar C-Glycosides to Introduce Diversity at C2 Position7 Conclusion

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“…Notably, the conversion of a primary alcohol to a carboxylic acid in the presence of a secondary alcohol may be more rapid than the oxidation of a secondary alcohol present in the substrate. Thus, a 1,2-diol was converted to an α-hydroxy carboxylic acid (Scheme 12.11) 76 or the primary alcohol on a tricyclic polyol was converted to an acid in the presence of a number of free and protected secondary and tertiary alcohols (Scheme 12.12), 77 or even allylic alcohols (Scheme 12.13). 78 The primary alcohol-to-carboxylic acid conversion can also be performed in a two-step, one-pot approach (Scheme 12.13).…”

Section: Oxidations Leading To Linear Carboxylic Acidsmentioning

confidence: 99%

Nitroxide‐Catalyzed Alcohol Oxidations in Organic Synthesis

Brückner

2010

Stable Radicals

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Synthesis of a bicyclic analog of l-iduronic acid adopting the biologically relevant 2 S 0 conformation

Cited by 10 publications

References 41 publications

Molecular engineering of glycosaminoglycan chemistry for biomolecule delivery

Molecular engineering of glycosaminoglycan chemistry for biomolecule delivery

Contributing to the Study of Enzymatic and Chemical Glycosyl Transfer Through the Observation and Mimicry of Glycosyl Cations

Nitroxide‐Catalyzed Alcohol Oxidations in Organic Synthesis

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