The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
2-Imino-2-methoxyethyl 1-thioglycosides: new reagents for attaching sugars to proteins
Abstract
Cyanomethyl 1-thioglycosides ofD-galactose, D-glucose, 2-acetamido-2-deoxy-D-glucose, and D-mannose were prepared from the respective pseudothiourea derivatives and chloroacetonitrile. The nitrile group in these cyanomethyl thioglycosides can be converted to a methyl imidate group by treatment with sodium methoxide or HC1 in dry methanol to yield 2-imino-2-methoxyethyl 1-thioglycosides (IME-thioglycosides). The factors influencing the yield of IME-thioglycosides were investigated. The most convenient method of preparing IME-thioglycosides was treating 0.1 M cyanomethyl thioglycoside peracetate in dry methanol with 0.01 M sodium methoxide at room temperature for 24-48 h (50-60% yield). These IME-thioglycosides reacted readily with simple amines, amino acids, and proteins in mildly alkaline buffer solutions. Alpha-amylase and lysozyme modified with these reagents under appropriate conditions retained full activities. Thus the IME-thioglycosides constitute a new group of reagents for attaching sugars to proteins.
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Citations
Cites
The Significance of Glycosylated Proteins
WINTERBURN, P. J., & PHELPS, C. F. (1972) · Nature · doi:10.1038/236147a0 · Cited by 213
Cited by
Stahl, P. D., Rodman, J. S., Miller, M. J., & Schlesinger, P. H. (1978) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.75.3.1399 · Cited by 590
Lee, Y. C., Townsend, R. R., Hardy, M. R., Lönngren, J., Arnarp, J., Haraldsson, M., & Lönn, H. (1983) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)33240-x · Cited by 503
Self-citationUptake of Pneumocystis carinii mediated by the macrophage mannose receptor
Ezekowitz, R. A. B., Williams, D. J., Koziel, H., Armstrong, M. Y. K., Warner, A., Richards, F. F., & Rose, R. M. (1991) · Nature · doi:10.1038/351155a0 · Cited by 448
Sando, G. N., & Neufeld, E. F. (1977) · Cell · doi:10.1016/0092-8674(77)90262-8 · Cited by 355
Metadata
- Authors
- Lee, Y. C., Stowell, C. P., & Krantz, M. J.
- Venue
- Biochemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1976-09-07
- Volume
- 15
- Issue
- 18
- Pages
- 3956-3963
- ISSN
- 0006-2960 (ISSN-L)
- 1520-4995
- OpenAlex
- W2067808410
- Cited by
- 335
- References
- 1
- FWCI
- 7.55
- Type
- journal article
- Language
- en
- Open access
- closed
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- Lee, Y. C., Stowell, C. P., & Krantz, M. J. (1976). 2-Imino-2-methoxyethyl 1-thioglycosides: new reagents for attaching sugars to proteins. Biochemistry. https://doi.org/10.1021/bi00663a008
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
