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Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate.

ABSTRACT: Alginate is a biocompatible and industrially relevant polysaccharide that derives many of its important properties from the charged carboxylate groups within its polyuronic acid backbone. The design and inclusion of isosteric replacements for these carboxylates would underpin provision of new oligo-/polysaccharide materials with alternate physicochemical properties. Presented herein is our synthesis of mannuronic acid building blocks, appropriately modified at the carboxylate C6 position with a bioisosteric tetrazole. Thioglycosides containing a protected C6-tetrazole are accessed from a C6-nitrile, through dipolar cycloaddition using NaN₃ with n-Bu₂SnO. We also demonstrate access to orthogonally C4-protected donors, suitable for iterative oligosaccharide synthesis. The development of these building blocks is showcased to access anomeric 3-aminopropyl- and 1-phosphate free sugars containing this non-native motif.

SUBMITTER: Dimitriou E

PROVIDER: S-EPMC8275867 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate.

Dimitriou Eleni E Miller Gavin J GJ

Beilstein journal of organic chemistry 20210705

Alginate is a biocompatible and industrially relevant polysaccharide that derives many of its important properties from the charged carboxylate groups within its polyuronic acid backbone. The design and inclusion of isosteric replacements for these carboxylates would underpin provision of new oligo-/polysaccharide materials with alternate physicochemical properties. Presented herein is our synthesis of mannuronic acid building blocks, appropriately modified at the carboxylate C6 position with a ...[more]

PMID: 34290835

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Project description:BackgroundAchieving equity of access to primary healthcare requires organizations to implement innovations tailored to the specific needs and abilities of vulnerable populations. However, designing pro-vulnerable innovations is challenging without knowledge of the range of possible innovations tailored to vulnerable populations' needs. To better support decision-makers, we aimed to develop a typology of pro-vulnerable organizational innovation components - akin to "building blocks" that could be combined in different ways into new complex innovations or added to existing organizational processes to improve access to primary healthcare.MethodsTo develop the typology, we used data from a previously conducted a) scoping review (2000-2014, searched Medline, Embase, CINAHL, citation tracking, n = 90 articles selected), and b) environmental scan (2014, online survey via social networks, n = 240 innovations). We conducted a typological analysis of the data. Our initial typology yielded 48 components, classified according to accessibility dimensions from the Patient-Centred Accessibility Framework. The initial typology was then field-tested for relevance and usability by health system stakeholders and refined from 2014 to 2018 (e.g., combined similar components, excluded non-organizational components).ResultsThe selected articles (n = 90 studies) and survey responses (n = 240 innovations) were mostly from the USA, Canada, Australia and the UK. Innovations targeted populations with various vulnerabilities (e.g., low income, chronic illness, Indigenous, homeless, migrants, refugees, ethnic minorities, uninsured, marginalized groups, mental illness, etc.). Our final typology had 18 components of organizational innovations, which principally addressed Availability & Accommodation (7/18), Approachability (6/18), and Acceptability (3/18). Components included navigation & information, community health worker, one-stop-shop, case management, group visits, defraying costs, primary healthcare brokerage, etc. CONCLUSIONS: This typology offers a comprehensive menu of potential components that can help inform the design of pro-vulnerable organizational innovations. Component classification according to the accessibility dimensions of the Patient-Centred Accessibility Framework is useful to help target access needs. Components can be combined into complex innovations or added to existing organizational processes to meet the access needs of vulnerable populations in specific contexts.

Dataset Information

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate.

Publications

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate.

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