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An improved installation of 2-hydroxy-4-methoxybenzyl(iHmb)method for chemical protein synthesis

Chinese Chemical Letters 2024年第5期35卷 145-150页

作者： Ying Li Long-Jie Wang Yong-Kang Zhou Jun Liang Bin Xiao Ji-Shen Zheng The First Affiliated Hospital of USTC MOE Key Laboratory for Membraneless Organelles and Cellular DynamicsDivision of Life Sciences and MedicineUniversity of Science and Technology of ChinaHefei 230001China Department of Chemistry University of Science and Technology of ChinaHefei 230027China

The 2-hydroxy-4-methoxybenzyl(Hmb)backbone modification can prevent amide bond-mediated sidereactions(e.g.,aspartimide formation,peptide aggregation)by installing the removable Hmb group into a peptide bond,thus improving the synthesis of long and challenging peptides and ***,its use is largely precluded by the limited Hmb’s installation *** this report,an improved installation of Hmb(iHmb)method was developed to achieve the flexible installation and the convenient removal of *** iHmb method involves two critical steps:(1)oxidative diazotization of the readily installed 2-hydroxy-4-methoxy-5-amino-benzyl(Hmab)to give 2-hydroxy-4-methoxy-5-diazonium-benzyl(Hmdab)by combining soamyl nitrite(IAN)/HBF_(4),and(2)reductive elimination of Hmdab to give the desired Hmb by 1,2-ethanedithiol(EDT).The iHmb method enables the installation of Hmb at any primary amino acid including the highly sterically hindered amino acids(e.g.,valine and isoleucine).The practicality and utility of the iHmb method was demonstrated by one-shot solid-phase synthesis of a challenging aspartimide-prone peptide,the mirror-image version of a hydrophobic peptide and a long-chain peptide up to ***,the iHmb method can be utilized to facilitate chemical protein ligation,as exemplified by the synthesis of the single-spanning membrane protein *** iHmb method expands the toolkit for peptide synthesis and ligation and facilitates the preparation of peptides/proteins.

关键词： Chemical protein synthesis solid-phase peptide synthesis Removable backbone modification 2-Hydroxy-4-methoxybenzyl(Hmb)group Aspartimide-prone peptides Difficult peptides Membrane proteins

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Recent advances in chemical protein synthesis:method developments and biological applications

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Science China Chemistry 2024年第4期67卷 1060-1096页

作者： Suwei Dong Ji-Shen Zheng Yiming Li Huan Wang Gong Chen Yongxiang Chen Gemin Fang Jun Guo Chunmao He Honggang Hu Xuechen Li Yanmei Li Zigang Li Man Pan Shan Tang Changlin Tian Ping Wang Bian Wu Chuanliu Wu Junfeng Zhao Lei Liu State Key Laboratory of Natural and Biomimetic Drugs and School of Pharmaceutical SciencesPeking UniversityBeijing 100191China Division of Life Sciences and Medicine University of Science and Technology of ChinaHefei 230027China School of Food and Biological Engineering Engineering Research Center of Bio-processMinistry of EducationHefei University of TechnologyHefei 230009China School of Chemistry and Chemical Engineering Nanjing UniversityNanjing 210023China State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China Department of Chemistry Tsinghua UniversityBeijing 100084China Institute of Health Sciences Anhui UniversityHefei 230601China College of Chemistry Central China Normal UniversityWuhan 430079China School of Chemistry and Chemical Engineering South China University of TechnologyGuangzhou 510640China School of Medicine or Institute of Translational Medicine Shanghai UniversityShanghai 200444China Department of Chemistry The University of Hong KongHong Kong 999077China Shenzhen Graduate School Peking UniversityShenzhen 518055China School of Chemistry and Chemical Engineering Shanghai Jiao Tong UniversityShanghai 200240China School of Life Sciences University of Science and Technology of ChinaHefei 230026China Department of Chemical Biology Shanghai Jiao Tong UniversityShanghai 200240China Institute of Microbiology Chinese Academy of SciencesBeijing 100101China Department of Chemistry Xiamen UniversityXiamen 361005China School of Pharmaceutical Science Guangzhou Medical UniversityGuangzhou 511436China

The central dogma of modern biology underscores the pivotal roles proteins play in diverse biological processes,the study of which necessitates advanced methods to produce proteins with precision and *** protein synthesis,a powerful approach utilizing chemical reactions for the de novo construction of structurally accurate proteins,has emerged as a transformative tool for studying proteins and generating protein derivatives/mimics inaccessible by natural biological machinery,including post-translationally modified proteins,proteins comprised of unnatural amino acids,as well as mirror-image *** review summarizes recent strides in synthetic method developments for chemical protein synthesis,including innovative techniques in solid-phase peptide synthesis,the challenges presented by difficult sequences in either synthesis or folding and the exploration of novel ligation reactions using both chemical and enzymatic ***,the review also delves into newly developed protocols for site-selective protein modifications and the generation of stapled or macrocyclized peptides/miniproteins,highlighting the power of chemical methods to make structurally diverse *** applications of synthetic proteins in investigating post-translational modifications(phosphorylation,lipidation,glycosylation,ubiquitination,etc.),mirror-image biological processes and drug development are further ***,these topics provide a comprehensive overview of the current landscape of chemical protein synthesis.

关键词： chemical protein synthesis solid-phase peptide synthesis ligation reactions post-translational modifications mirror-image proteins peptide drugs

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Exploiting Complex-Type N-Glycan to Improve the in Vivo Stability of Bioactive peptides

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CCS Chemistry 2023年第7期5卷 1623-1634页

作者： Qijia Wei Jun Zhang Yuankun Dao Mengliang Ye Dangliang Liu Weidong Dong Ning Yuan Hongxing Li Chunli Song Mo Li Xiaomeng Shi Suwei Dong State Key Laboratory of Natural and Biomimetic Drugs Peking UniversityBeijing 100191 Chemical Biology Center Peking UniversityBeijing 100191 Department of Chemical Biology School of Pharmaceutical SciencesPeking UniversityBeijing 100191 Department of Orthopedics Peking University Third HospitalBeijing 100191 Center for Reproductive Medicine Department of Obstetrics and GynecologyPeking University Third HospitalBeijing 100191 National Clinical Research Center for Obstetrics and Gynecology Peking University Third HospitalBeijing 100191 Beijing Key Laboratory of Reproductive Endocrinology and Assisted Reproductive Technology Peking University Third HospitalBeijing 100191

peptides can be potentmolecules with high efficacy and selectivity in the development of ***,the poor pharmacokinetic properties of peptides pose major challenges for their broader medicinal *** by the proteinstabilizing role of natural N-glycosylation,we design and synthesize a series of parathyroid hormone(PTH)peptides(1-34),bearing either N-GlcNAc or biantennary complex-type N-glycan modification,and evaluate their serum stability and biological *** results indicate that an N-Asn-linked complex-type sialylundecasaccharide can increase the serum half-life and in vivo bioactivity of PTH peptides with a broad tolerance of modification ***,hydrogen/deuterium exchange mass spectroscopy indicates that the larger-sized Nglycan can induce enhanced hydration dynamics in its surroundings,which may facilitate an improved resistance for the peptide against enzymatic *** sialylundecasaccharide-based peptideengineering strategy has also been applied to glucagon-like peptide-1(7-37),leading to glycopeptides with enhanced hypoglycemic activity and acting time in ***,these results demonstrate the potential of using sialylated complextype N-glycan as a general engineering strategy for developing long-acting peptide therapeutics.

关键词： therapeutic peptides stability Nglycosylation solid-phase peptide synthesis chemoenzymatic approach hydrogen-deuterium exchange mass spectrometry

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An expedient synthesis of peptidyl N-alkylamides by "HOPE" strategy

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Chinese Chemical Letters 2012年第5期23卷 565-568页

作者： Hao Lin Xiao Xiao Yang De Xin Wang Institute of Materia Medica Chinese Academy of Medical Sciences&Peking Union Medical CollegeBeijing Key Laboratory of Active Substance Discovery and Druggability Evaluation Beijing 100050China

We have developed an expedient approach,＂HOPE＂（hybrid orthogonal protocol with ease） strategy for the synthesis of peptidyl *** new strategy was characterized by following points：incorporating Boc and Fmoc protocols together on Merrifield resin,removal of SPG（side-chain protecting groups） without the damage of linker structure on the resin,and the ammonolysis of linker as the last step could achieve the introducing N-alkylamide structure into C-terminal and releasing product from resin-support *** present work,eight peptidylamides with different alkylsubstitution at C-terminal were conveniently synthesized by HOPE strategy.

关键词： "HOPE" strategy solid-phase peptide synthesis Peptidyl N-alkylamide

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Total synthesis of TRADD death domain with arginine N-GlcNAcylation by hydrazide-based native chemical ligation

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Chinese Chemical Letters 2020年第1期31卷 107-110页

作者： Ye Wu Yulei Li Wei Cong Yan Zou Xiang Li Honggang Hu Institute of Translational Medicine Shanghai UniversityShanghai 200436China School of Pharmacy Second Military Medical UniversityShanghai 200433China Key Laboratory of Marine Drugs Ministry of EducationSchool of Medicine and PharmacyOcean University of ChinaQingdao 266003China

TNFR1-associated death domain protein(TRADD)with arginine N-GlcNAcylation is a novel and structurally unique posttranslational modification(PTM)glycoprotein that blocks the formation of death-inducing signaling complex(DISC),orchestrating host nuclear factorκB(NF-κB)signaling in entero-pathogenic Escherichia coli(EPEC)-infected *** particular glycosylated modification plays an extremely vital role for the effective colonization and pathogenesis of pathogens in the *** we describe the total synthesis of TRADD death domain(residues 195-312)with arginine235 NGlcNAcylation(Arg-GIcNAc TRADD(195-312)).Two longish peptidyl fragments of the wild-type primary sequence were obtained by robust,microwave-assisted,highly efficient,solid-phase peptide synthesis(SPPS),the N-GlcNAcylated sector was built by total synthesis and attached specifically to resinbound peptide with an unprotected ornithine residue via silver-promoted on-resin guanidinylation,ArgGlcNAc TRADD(195-312)was constructed by hydrazide-based native chemical ligation(NCL).The facile synthetic strategy is expected to be generally applicable for the rapid synthesis of other proteins with Arg-GIcNAc modification and to pave the way for the related chemically biological study.

关键词： TRADD death domain Posttranslational modification Protein chemical synthesis solid-phase peptide synthesis Native chemical ligation peptide hydrazide

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An Improved synthesis of Laminin Fragment CR9

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Chinese Chemical Letters 2002年第12期13卷 1154-1157页

作者： Gui Jie TIAN Shi Jun LI De Xin WANG Institute of Materia Medica Chinese Academy of Medical SciencesBeijing 100050

Laminin nonapeptide CR9 was synthesized via two different methods. A notably enhanced yield (46.8%) was obtained from method B compared to that (12.4%) from standard protocol (method A).

关键词： solid-phase peptide synthesis MBHA resin Pac resin.

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