Synthesis of Disulfide Surrogate Peptides through a Serine/Threonine Ligation-Assisted Diaminodiacid Strategy.

We report a new serine/threonine ligation (STL)-assisted diaminodiacid (DADA) strategy for the flexible construction of disulfide surrogates by the option of more abundant -Aa-Ser/Thr- ligation sites. The practicality of this strategy was evidenced by the synthesis of the intrachain disulfide surrogate of C-type natriuretic peptide and the interchain disulfide surrogate of insulin.

[1]  C. Tian,et al.  Single-Shot Solid-Phase Synthesis of Full-Length H2 Relaxin Disulfide Surrogates. , 2022, Angewandte Chemie.

[2]  Han Liu,et al.  Chemical Synthesis of Proteins with Base-labile Posttranslational Modifications Enabled by a Boc-SPPS Based General Strategy Towards Peptide C-terminal Salicylaldehyde Esters. , 2022, Angewandte Chemie.

[3]  Xianbin Meng,et al.  Photocaging of Activity-based Ubiquitin Probes via a C-Terminal Backbone Modification Strategy. , 2022, Angewandte Chemie.

[4]  Han Liu,et al.  Total Synthesis of Mannopeptimycin β via β-Hydroxyenduracididine Ligation. , 2021, Journal of the American Chemical Society.

[5]  C. Tian,et al.  The New Salcylaldehyde S,S-Propanedithioacetal Ester Enables N-to-C Sequential Native Chemical Ligation and Ser/Thr Ligation for Chemical Protein Synthesis. , 2020, Journal of the American Chemical Society.

[6]  Lei Liu,et al.  Synthesis of disulfide surrogate peptides incorporating large-span surrogate bridges through a native chemical ligation-assisted diaminodiacid strategy. , 2020, Angewandte Chemie.

[7]  Chengjie Sun,et al.  Self-Assembly of Constrained Cyclic Peptides Controlled by Ring Size , 2020 .

[8]  C. Jaxel,et al.  Chemical Synthesis of Native S-palmitoylated Membrane Proteins through Reversible Backbone Modification Assisted Ser/Thr Ligation. , 2019, Angewandte Chemie.

[9]  Lei Liu,et al.  Cysteine-Aminoethylation-Assisted Chemical Ubiquitination of Recombinant Histones. , 2019, Journal of the American Chemical Society.

[10]  D. Bierer,et al.  Synthesis of Peptide Disulfide-Bond Mimics by Using Fully Orthogonally Protected Diaminodiacids. , 2018, Organic letters.

[11]  Han Liu,et al.  Serine/Threonine Ligation: Origin, Mechanistic Aspects, and Applications. , 2018, Accounts of chemical research.

[12]  J. Bode.  Chemical Protein Synthesis with the α-Ketoacid-Hydroxylamine Ligation. , 2017, Accounts of chemical research.

[13]  L. Moroder,et al.  Insulin-From its Discovery to the Industrial Synthesis of Modern Insulin Analogues. , 2017, Angewandte Chemie.

[14]  James C. Collins,et al.  The Current State of Peptide Drug Discovery: Back to the Future? , 2017, Journal of medicinal chemistry.

[15]  Han Liu,et al.  Enabling N-to-C Ser/Thr Ligation for Convergent Protein Synthesis via Combining Chemical Ligation Approaches. , 2016, Journal of the American Chemical Society.

[16]  J. Mayer,et al.  Pursuit of a perfect insulin , 2016, Nature Reviews Drug Discovery.

[17]  Lei Liu,et al.  Diaminodiacid Bridges to Improve Folding and Tune the Bioactivity of Disulfide-Rich Peptides. , 2015, Angewandte Chemie.

[18]  Lei Liu,et al.  Peptide o-aminoanilides as crypto-thioesters for protein chemical synthesis. , 2015, Angewandte Chemie.

[19]  Miriam Góngora-Benítez,et al.  Multifaceted roles of disulfide bonds. Peptides as therapeutics. , 2014, Chemical reviews.

[20]  C. Tian,et al.  Diaminodiacid-based solid-phase synthesis of peptide disulfide bond mimics. , 2013, Angewandte Chemie.

[21]  R. Norton,et al.  Dicarba α-conotoxin Vc1.1 analogues with differential selectivity for nicotinic acetylcholine and GABAB receptors. , 2013, ACS chemical biology.

[22]  Xuechen Li,et al.  Protein chemical synthesis by serine and threonine ligation , 2013, Proceedings of the National Academy of Sciences.

[23]  Lei Liu,et al.  Convergent chemical synthesis of proteins by ligation of peptide hydrazides. , 2012, Angewandte Chemie.

[24]  J. Bode,et al.  Chemical protein synthesis by chemoselective α-ketoacid-hydroxylamine (KAHA) ligations with 5-oxaproline. , 2012, Angewandte Chemie.

[25]  D. Craik,et al.  α-Conotoxin ImI incorporating stable cystathionine bridges maintains full potency and identical three-dimensional structure. , 2011, Journal of the American Chemical Society.

[26]  Lei Liu,et al.  Protein chemical synthesis by ligation of peptide hydrazides. , 2011, Angewandte Chemie.

[27]  A. Hobbs,et al.  C-type natriuretic peptide (CNP): cardiovascular roles and potential as a therapeutic target. , 2010, Current pharmaceutical design.

[28]  J. Vederas,et al.  Antimicrobial leucocin analogues with a disulfide bridge replaced by a carbocycle or by noncovalent interactions of allyl glycine residues. , 2006, Journal of the American Chemical Society.

[29]  Jui-Yoa Chang,et al.  Conformational impurity of disulfide proteins: detection, quantification, and properties. , 2005, Analytical biochemistry.

[30]  H. Mitani,et al.  Four functionally distinct C-type natriuretic peptides found in fish reveal evolutionary history of the natriuretic peptide system , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[31]  H. Scheraga,et al.  Disulfide bonds and protein folding. , 2000, Biochemistry.

[32]  T. Muir,et al.  Synthesis of proteins by native chemical ligation. , 1994, Science.