# Methods and Mechanisms in Carbohydrate Chemistry

> **NIH NIH R01** · UNIVERSITY OF GEORGIA · 2020 · $294,898

## Abstract

Although glycochemistry has developed in leaps and bounds in the last two decades,
the synthesis of a complex oligosaccharide or of a glycoconjugate remains a very
challenging albeit critically important task. The difficulties inherent in such syntheses
arise because of numerous reasons that center on the complexity of the chemistry when
compared to that of oligonucleotide and peptide synthesis. The most important
reactions in any oligosaccharide synthesis are the formation of the glycosidic bonds and
there exists an absolutely overwhelming number of methods toward this end.
Unfortunately, the vast majority of these methods have been developed empirically, are
therefore underpinned by very little detailed understanding of mechanism, and have very
little generality.
 The underlying theme of this proposal is that the challenge of the simplification of
complex oligosaccharide synthesis is best met by an improved understanding of the
mechanisms of glycosidic bond formation, coupled with the development of more
efficient, straightforward and general mechanism-based methods. A necessary step
toward this goal is the detailed investigation of the mechanisms of glycosylation
mechanisms, and accordingly this proposal addresses several issues considered critical
to the resolution of this problem. The issues to be addressed include i) the development
of cation clock methods for the determination of reaction kinetics in sialic acid and
furanoside glycosidic bond formation. ii) The determination of the interplay of the side
chain conformation and of protecting groups and their combined influence on
glycosylation stereoselectivity. iii) The development of methods for the efficient
synthesis of the microbial sialic acids, legionaminic acid and pseudaminic acid, and of
their glycosides. iv) The development of novel methods for the synthesis of C5 modified
sialic acids by stereocontrolled substitutive deamination.

## Key facts

- **NIH application ID:** 9869012
- **Project number:** 5R01GM062160-20
- **Recipient organization:** UNIVERSITY OF GEORGIA
- **Principal Investigator:** David Crich
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2020
- **Award amount:** $294,898
- **Award type:** 5
- **Project period:** 2001-09-30 → 2021-08-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/9869012

## Citation

> US National Institutes of Health, RePORTER application 9869012, Methods and Mechanisms in Carbohydrate Chemistry (5R01GM062160-20). Retrieved via AI Analytics 2026-06-10 from https://api.ai-analytics.org/grant/nih/9869012. Licensed CC0.

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