Two-Step Functionalization of Oligosaccharides Using Glycosyl Iodide and Trimethylene Oxide and Its Applications to Multivalent Glycoconjugates

Hsieh, Hsiao-Wu; Davis, Ryan A.; Hoch, Jessica A.; Gervay-Hague, Jacquelyn

doi:10.1002/chem.201400024

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Two-Step Functionalization of Oligosaccharides Using Glycosyl Iodide and Trimethylene Oxide and Its Applications to Multivalent Glycoconjugates

5 19 2014
By Hsieh, Hsiao-Wu ; Davis, Ryan A. ; Hoch, Jessica A. ; ...
http://dx.doi.org/10.1002/chem.201400024
Source: Chemistry. 2014; 20(21):6444-6454

[PDF-2.00 MB]

English

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Details:

Alternative Title:

Chemistry
Personal Author:

Hsieh, Hsiao-Wu ; Davis, Ryan A. ; Hoch, Jessica A. ; Gervay-Hague, Jacquelyn

Hsieh, Hsiao-Wu ; Davis, Ryan A. ; Hoch, Jessica A. ; Gervay-Hague, Jacquelyn Less -
Description:

Oligosaccharide conjugates, such as glycoproteins and glycolipids, are potential chemotherapeutics and also serve as useful tools for understanding the biological roles of carbohydrates. With many modern isolation and synthetic technologies providing access to a wide variety of free sugars, there is increasing need for general methodologies for carbohydrate functionalization. Herein, we report a two-step methodology for the conjugation of per-O-acetylated oligosaccharides to functionalized linkers that can be used for various displays. Oligosaccharides obtained from both synthetic and commercial sources were converted to glycosyl iodides and activated with I2 to form reactive donors that were subsequently trapped with trimethylene oxide to form iodopropyl conjugates in a single step. The terminal iodide served as a chemical handle for further modification. Conversion into the corresponding azide followed by copper-catalyzed azide-alkyne cycloaddition afforded multivalent glycoconjugates of Gb3 for further investigation as anti-cancer therapeutics.
Subjects:

[+]

Carbohydrates Glycoconjugates Glycosylation Humans Iodides Molecular Structure Oligosaccharides
Keywords:

[+]

Carbohydrates Functionalization Glycosylation Glycosyl Iodides Multivalent Glycoconjugates
Source:

Chemistry. 2014; 20(21):6444-6454
Pubmed ID:

24715520
Pubmed Central ID:

PMC4497529
Document Type:

Journal Article
Funding:

R01 GM090262/GM/NIGMS NIH HHSUnited States/ ; PR1973/PR/OCPHP CDC HHSUnited States/ ; R01 M090262/PHS HHSUnited States/

R01 GM090262/GM/NIGMS NIH HHSUnited States/ ; PR1973/PR/OCPHP CDC HHSUnited States/ ; R01 M090262/PHS HHSUnited States/ Less -
Volume:

20
Issue:

21
Collection(s):

CDC Public Access
Main Document Checksum:

[+]

urn:sha256:8b59aeb91b6c8dca6e30a7d9008445afef6e30b6e17a2e6c85b6362fd0efd83a
Download URL:

https://stacks.cdc.gov/view/cdc/32043/cdc_32043_DS1.pdf
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