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Research Spending & Results

Award Detail

Awardee:SAINT LOUIS UNIVERSITY
Doing Business As Name:Saint Louis University
PD/PI:
  • Alexei V Demchenko
  • (314) 516-7995
  • demchenkoa@umsl.edu
Award Date:08/25/2021
Estimated Total Award Amount: $ 450,000
Funds Obligated to Date: $ 149,995
  • FY 2018=$149,995
Start Date:09/01/2021
End Date:08/31/2022
Transaction Type:Grant
Agency:NSF
Awarding Agency Code:4900
Funding Agency Code:4900
CFDA Number:47.049
Primary Program Source:040100 NSF RESEARCH & RELATED ACTIVIT
Award Title or Description:Stereoselective glycosylation via H-bond-mediated aglycone delivery
Federal Award ID Number:2147156
DUNS ID:050220722
Parent DUNS ID:050220722
Program:Chemical Synthesis
Program Officer:
  • Jin Cha
  • (703) 292-2461
  • jcha@nsf.gov

Awardee Location

Street:221 N. Grand Blvd.
City:St Louis
State:MO
ZIP:63103-2006
County:Saint Louis
Country:US
Awardee Cong. District:01

Primary Place of Performance

Organization Name:Saint Louis University
Street:
City:
State:MO
ZIP:63103-2006
County:Saint Louis
Country:US
Cong. District:01

Abstract at Time of Award

The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Alexei Demchenko. Professor Demchenko is a faculty member in the Department of Chemistry and Biochemistry at the University of Missouri - St. Louis. Professor Demchenko's research group is developing new methods for accomplishing reactions that hook two sugar molecules together. These reactions, called glycosylations, are essentially for assembling the types of carbohydrate structures that are prevalent in a wide range of biological processes and applications of the glycolsylation reactions being developed range from therapeutic to diagnostic strategies. Key to the effort is work both better understand and further develop a unique reaction pathway that was discovered by the Demchenko group during the previous funding period. This discovery is enabling the construction on the bond connecting the two sugars in a highly selective manner. The project lies at the interface of organic, carbohydrate, and mechanistic chemistry, and it is well suited for the education of scientists at all levels. This study is investigating both mechanistic and practical aspects of the H-bond-mediated Aglycone Delivery (HAD) reaction pathway discovered by the PI's group. The goal of the work is to completely control the stereoselectivity of the glycosylation. With this in mind, two phenomena are being investigated. In the first, two previously developed methods, bromine-promoted glycosylation and HAD reaction are being combined in a manner that affords higher stereoselectivity for both alpha- and beta-glycosylation. In the second, conformational switches are being developed as handles for enhancing the utility of the HAD reaction. These endeavors are strategically advancing the field of glycosciences by offering new synthetic capabilities for obtaining challenging glycans and glycoconjugates with better stereocontrol and higher yields. The developed methods are serving to improve the synthesis of key targets from mammalian glycomes and microbial glycans with potential application as therapeutic agents or diagnostic platforms. Successful completion of the proposed research is not only advancing the field of glycosylation, but is also making contributions to the larger chemical, biological, and medical sciences. Integral to the success of this program is the active participation of undergraduate and graduate students who receive solid training in research methods and work to solve synthetic important synthetic challenges. The vigorous training and strong publication and presentation records that students are gaining in the PI's laboratory is preparing them for leading positions in academia and industry. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

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