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Chemical Synthesis of a Glycoprotein Having an Intact Human Complex-Type Sialyloligosaccharide under the Boc and Fmoc Synthetic Strategies
Abstract
The chemical synthesis of complex glycoproteins is an ongoing challenge in protein chemistry. We have examined the synthesis of a single glycoform of monocyte chemotactic protein-3 (MCP-3), a CC-chemokine that consists of 76 amino acids and one N-glycosylation site. A three-segment native chemical ligation strategy was employed using unprotected peptides and glycopeptide. Importantly, the synthesis required the development of methods for the generation of sialylglycopeptide-alphathioesters. For the sialylglycopeptide-alphathioester segment, we examined and successfully implemented approaches using Fmoc-SPPS and Boc-SPPS. To avoid use of hydrogen fluoride, the Boc approach utilized minimal side chain protection and direct thiolysis of the resin bound peptide. Using these strategies, we successfully synthesized a glycoprotein having an intact and homogeneous complex-type sialyloligosaccharide.
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Cites
Intracellular Functions of N-Linked Glycans
Helenius, A., & Aebi, A. M. (2001) · Science · doi:10.1126/science.291.5512.2364 · Cited by 2,405
Roles of N-Linked Glycans in the Endoplasmic Reticulum
Helenius, A., & Aebi, M. (2004) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.73.011303.073752 · Cited by 2,037
Cited by
Enzymes in the Synthesis of Glycoconjugates
Schmaltz, R. M., Hanson, S. R., & Wong, C.-H. (2011) · Chemical Reviews · doi:10.1021/cr200113w · Cited by 283
Protein chemical synthesis by serine and threonine ligation
Zhang, Y., Xu, C., Lam, H. Y., Lee, C. L., & Li, X. (2013) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1221012110 · Cited by 272
Metadata
- Authors
- Yamamoto, N., Tanabe, Y., Okamoto, R., Dawson, P. E., & Kajihara, Y.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-12-18
- Volume
- 130
- Issue
- 2
- Pages
- 501-510
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1974599312
- Cited by
- 159
- References
- 2
- FWCI
- 9.83
- Type
- journal article
- Language
- en
- Open access
- closed
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- Yamamoto, N., Tanabe, Y., Okamoto, R., Dawson, P. E., & Kajihara, Y. (2008). Chemical Synthesis of a Glycoprotein Having an Intact Human Complex-Type Sialyloligosaccharide under the Boc and Fmoc Synthetic Strategies. Journal of the American Chemical Society. https://doi.org/10.1021/ja072543f
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Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
