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Progress in Chemistry 2023, Vol. 35 Issue (11): 1579-1594 DOI: 10.7536/PC230325 Previous Articles   Next Articles

• Review •

Segment Solubilizing Strategy in Protein Chemical Synthesis

Deng Xiangyu1,2, Zhang Baochang1, Qu Qian2()   

  1. 1 Tsinghua University Tsinghua-Peking Center for Life Sciences, Ministry of Education Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, State Key Laboratory of Chemical Oncogenomics (Shenzhen), Department of Chemistry,Beijing 100084, China
    2 Shanghai Jiao Tong University Institute of Translational Medicine,Shanghai 200240, China
  • Received: Revised: Online: Published:
  • Contact: Qu Qian
  • Supported by:
    National Natural Science Foundation of China(22277073)
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Proteins play critical roles in various biological processes and biomedical researches. A significant task of such biochemical studies is to obtain protein samples of high homogeneity with respect to their atomic compositions. Chemical protein synthesis offers a much more robust and effective strategy over recombinant expression technology for accessing proteins that are precisely modified or even artificially designed. However, some important proteins that can be used as drug targets (such as human interleukin-2, K+ channel protein Kir5.1, etc.) suffer from limited solubility of peptide segments during the journey of protein synthesis. Such hydrophobic peptides pose difficulty for subsequent purification, characterization, chemical ligation and other operations. The main factors for these problems may be that the peptide segments are prone to self-assemble into secondary structures through hydrophobic interactions, hydrogen bond or other interaction modes, thus reducing the solubility. Addition of solubilizing tags is recognized as one of the effective methods to overcome such obstacles. In this review, strategies of attaching solubilizing tags to the main chain, side chain and backbone of peptides are introduced. Membrane protein FCER1G, co-chaperone protein GroES and other proteins are selected as examples to describe the applications of the solubilizing tags. Moreover, the future of solubilizing tags strategy is discussed and prospected.

Contents

1 Introduction

2 Main chain solubilizing tags

2.1 C-terminal solubilizing tags

2.2 N-terminal solubilizing tags

3 Side chain solubilizing tags

3.1 Cysteine (Cys) side chain solubilizing tags

3.2 Lysine (Lys) side chain solubilizing tags

3.3 Asparagine (Asn) /Glutamine (Gln) side chain solubilizing tags

4 Backbone modifications as solubilizing tags

4.1 Irreversible backbone modification

4.2 Removable backbone modification

5 Conclusion and outlook

Key words: chemical protein synthesis, peptide, native chemical ligation, segment solubilizing strategy, hydrophobic interactions
Fig.1 Reasons for poor solubility of peptide fragments[56]
Fig.2 Methods for improving the solubility of peptides[57⇓⇓⇓⇓⇓~63]
Scheme 1 C terminal thioester solubilizing tag[67]
Fig.3 Division of DGK hydrophilic peptides[67]
Fig.4 Other C-terminal solubilizing tags[70⇓~72]
Fig.5 N-terminal solubilizing tags[73,74]
Scheme 2 Base-liable N-terminal solubilizing tags[73]
Fig.6 Side chain-based solubilizing tags
Scheme 3 Cys side chain solubilizing strategy developed by Brik et al[78]
Scheme 4 Total chemical synthesis of histone H4[78]
Scheme 5 Cys side chain solubilizing strategy developed by Yoshiya et al[81]
Scheme 6 Total chemical synthesis of CP149[81]ALC
Scheme 7 Cys side chain solubilizing strategy developed by Deber et al[84]
Scheme 8 Cys side chain solubilizing strategy developed by Li et al[85]
Scheme 9 Total chemical synthesis of membrane protein FCER1G[85]
Scheme 10 Lys side chain solubilizing strategy developed by Danishefsky et al[89]
Scheme 11 Optimization of physical and chemical properties of hEPO peptide fragment[89]
Scheme 12 Lys side chain solubilizing strategy developed by Hojo et al[91]
Scheme 13 Total chemical synthesis of IL-2[91]
Scheme 14 Lys side chain solubilizing strategy developed by Kay et al[94]
Scheme 15 Total chemical synthesis of GroES[94]
Fig.7 The structure of Ddap[96]
Scheme 16 Lys side chain solubilizing strategy developed by Yoshiya et al[97]
Scheme 17 Strategy developed by Imperial et al[99]
Scheme 18 Gln side chain solubilizing strategy developed by Liu et al[100]
Scheme 19 Total chemical synthesis of LC3-Ⅱ[100]
Fig.8 Irreversible backbone modification[102]
Fig.9 Hmb and its derivatives[104,105]
Scheme 20 The RBM strategy[56,106]
Scheme 21 Total chemical synthesis of p7 ion channel[106]
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