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Staudinger Ligation: A Peptide from a Thioester and Azide
Abstract
[reaction: see text] The technique of native chemical ligation enables the total chemical synthesis of proteins. This method is limited, however, by an absolute requirement for a cysteine residue at the ligation juncture. Here, this restriction is overcome with a new chemical ligation method in which a phosphinobenzenethiol is used to link a thioester and azide. The product is an amide with no residual atoms.
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Citations
Cited by
Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality
Sletten, E. M., & Bertozzi, C. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200900942 · Cited by 3,165
Prescher, J. A., & Bertozzi, C. R. (2005) · Nature Chemical Biology · doi:10.1038/nchembio0605-13 · Cited by 1,456
Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations
Agouridas, V., El Mahdi, O., Diemer, V., Cargoët, M., Monbaliu, J.-C. M., & Melnyk, O. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00712 · Cited by 650
Expanding the chemical toolbox for the synthesis of large and uniquely modified proteins
Bondalapati, S., Jbara, M., & Brik, A. (2016) · Nature Chemistry · doi:10.1038/nchem.2476 · Cited by 359
Umpolung reactivity in amide and peptide synthesis
Shen, B., Makley, D. M., & Johnston, J. N. (2010) · Nature · doi:10.1038/nature09125 · Cited by 318
Metadata
- Authors
- Nilsson, B. L., Kiessling, L. L., & Raines, R. T.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-06-01
- Volume
- 2
- Issue
- 13
- Pages
- 1939-1941
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W1984574571
- Cited by
- 533
- References
- 0
- FWCI
- 2.70
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Staudinger Ligation: A Peptide from a Thioester and Azide. https://app.cochat.ai/papers/10.1021/ol0060174
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- Nilsson, B. L., Kiessling, L. L., & Raines, R. T. (2000). Staudinger Ligation: A Peptide from a Thioester and Azide. Organic Letters. https://doi.org/10.1021/ol0060174
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