Cooperative Stapling of Native Peptides at Lysine and Tyrosine or Arginine with Formaldehyde
Bo Li
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorHong Tang
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorDr. Aneta Turlik
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095 USA
Search for more papers by this authorZhao Wan
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorProf. Dr. Xiao-Song Xue
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095 USA
Search for more papers by this authorProf. Dr. Li Li
Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorDr. Xiaoxiao Yang
Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorDr. Jiuyuan Li
Asymchem Life Science Co., Ltd. TEDA, Tianjin, 300457 China
Search for more papers by this authorProf. Dr. Gang He
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Kendall N. Houk
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Gong Chen
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorBo Li
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorHong Tang
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorDr. Aneta Turlik
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095 USA
Search for more papers by this authorZhao Wan
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorProf. Dr. Xiao-Song Xue
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095 USA
Search for more papers by this authorProf. Dr. Li Li
Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorDr. Xiaoxiao Yang
Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorDr. Jiuyuan Li
Asymchem Life Science Co., Ltd. TEDA, Tianjin, 300457 China
Search for more papers by this authorProf. Dr. Gang He
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Kendall N. Houk
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Gong Chen
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorDedicated to Professor Samuel J. Danishefsky
Abstract
Stapling of peptides by intramolecular crosslinking of two neighboring amino acid side chains offers an important tool to modulate the structure and properties of peptides. In comparison to the stapling of artificially engineered peptide substrates, methods for stapling native peptides are more desirable for easier accessibility and genetic encodability. However, the existing strategy for selectivity control in the stapling of native peptides is relatively limited: the site of anchoring is often dominated by Cys, and the means for achieving the position selectivity among the same type of residues at different locations is lacking. We have developed a simple and powerful strategy for stapling native peptides at lysine residues with formaldehyde by the cooperation of nearby tyrosine or arginine residues. The stapling reactions can proceed with high efficiency and residue selectivity under mild conditions, and generate linchpins with distinct physiochemical properties. The new method for peptide stapling enables unique control of position-selectivity for substrates bearing multiple reaction sites by reactivity that can be readily built in the peptide sequence.
Conflict of interest
The authors declare no conflict of interest.
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