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Extending Synthetic Access to Proteins with a Removable Acyl Transfer Auxiliary
Abstract
A chemo- and regioselective auxiliary-mediated peptide ligation has been developed that is effective under nonidealized conditions for the synthesis of proteins. This general amide bond ligation utilizes a removable auxiliary that is analogous to the role of cysteine in native chemical ligation, combining chemoselective thioester exchange with efficient regioselective intramolecular acyl transfer. Acid lability and improved ligation efficiency were introduced into the 2-mercaptobenzyl auxiliary by increasing the electron density of the aromatic ring. The 62 amino acid SH3 domain from alpha-spectrin was synthesized using the auxiliary-mediated ligation at a Lys-Gly sequence. The auxiliary was removed with TFA and scavengers from the ligated product. This methodology enables unprotected peptides to be coupled at noncysteine ligation sites expanding the scope of protein synthesis and semisynthesis.
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Cited by
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
Blanco‐Canosa, J. B., & Dawson, P. E. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705471 · Cited by 512
Self-citationExpanding 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
Chemical Synthesis of Proteins
Nilsson, B. L., Soellner, M. B., & Raines, R. T. (2005) · Annual Review of Biophysics and Biomolecular Structure · doi:10.1146/annurev.biophys.34.040204.144700 · Cited by 329
Native Chemical Ligation at Phenylalanine
Crich, D., & Banerjee, A. (2007) · Journal of the American Chemical Society · doi:10.1021/ja072804l · Cited by 282
Metadata
- Authors
- Offer, J., Boddy, C. N. C., & Dawson, P. E.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-04-05
- Volume
- 124
- Issue
- 17
- Pages
- 4642-4646
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2082022880
- Cited by
- 276
- References
- 0
- FWCI
- 3.67
- Type
- journal article
- Language
- en
- Open access
- closed
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- Offer, J., Boddy, C. N. C., & Dawson, P. E. (2002). Extending Synthetic Access to Proteins with a Removable Acyl Transfer Auxiliary. Journal of the American Chemical Society. https://doi.org/10.1021/ja016731w
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