# Selective Catalytic Strategies for Carbohydrate Synthesis

> **NIH NIH R01** · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · 2024 · $292,712

## Abstract

Project Summary
Rare and unnatural carbohydrates play an essential role in the potency and selectivity of hundreds of bioactive
natural products and pharmaceutical compounds. These scaffolds often feature unusual relative/absolute
stereochemistry, pyranose/furanose ring branching, heteroatom substitutions, and varying degrees of
deoxygenation. Despite the biological significance of rare and unnatural sugars, synthetic challenges limit access
to these important molecules. Due to their functional group density and stereochemical complexity, current
syntheses of rare and unnatural sugars require multistep chemical synthesis, and commonly rely on protecting
group manipulations to achieve selective reaction outcomes. New, selective methods are needed for the
expedient synthesis of pyranose and furanose sugars. This proposal describes the development of selective
radical reactions to transform unprotected and minimally protected carbohydrates into diversely functionalized
monosaccharides and glycans. We specifically target epimerization reactions and radical rearrangements to
achieve broad synthetic access to rare isomeric and deoxygenated sugars, respectively. Using state-of-the-art
synthetic, mechanistic and theoretical tools, our approach involves the identification of new catalytic strategies
to control bond breaking, bond forming, and radical reorganization steps within the context of complex glycan
molecular frameworks. The successful development of this proposed research is anticipated to transform
carbohydrate synthesis, dramatically reducing the time and resources necessary to access these complex
pharmacophores. Fundamental mechanistic findings revealed en route to this goal are further anticipated to
contribute significantly to our understanding of carbohydrate reactivity patterns and to lay the groundwork for
catalytic approaches to selective radical functionalization reactions, more broadly.

## Key facts

- **NIH application ID:** 10783023
- **Project number:** 5R01GM141275-03
- **Recipient organization:** MASSACHUSETTS INSTITUTE OF TECHNOLOGY
- **Principal Investigator:** Alison Wendlandt
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2024
- **Award amount:** $292,712
- **Award type:** 5
- **Project period:** 2022-04-01 → 2026-01-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10783023

## Citation

> US National Institutes of Health, RePORTER application 10783023, Selective Catalytic Strategies for Carbohydrate Synthesis (5R01GM141275-03). Retrieved via AI Analytics 2026-05-26 from https://api.ai-analytics.org/grant/nih/10783023. Licensed CC0.

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