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Tetrazine bioorthogonal click-to-release reaction for releasing peptides
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Xiao-meng WANG1, Jie LI2, Guo-hua SHEN1, Li-li PAN1, Rong TIAN1, Hong-bao SUN2, *, Hao-xing WU2, *
Acta Pharmaceutica Sinica | 2020, 55(7) : 1634 - 1646
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Acta Pharmaceutica Sinica | 2020, 55(7): 1634-1646
• Original Articles •
Tetrazine bioorthogonal click-to-release reaction for releasing peptides
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Xiao-meng WANG1, Jie LI2, Guo-hua SHEN1, Li-li PAN1, Rong TIAN1, Hong-bao SUN2, *, Hao-xing WU2, *
Affiliations
  • 1. Department of Nuclear Medicine, West China Hospital, Sichuan University, Chengdu 610041, China
  • 2. Huaxi MR Research Center, West China Hospital, Sichuan University, Chengdu 610041, China
Published: 2020-07-12 doi: 10.16438/j.0513-4870.2020-0139
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This paper aimed to investigate the release efficiency of peptide at carbon terminal triggered by tetrazine bioorthogonal click-to-release reaction, and further explored the potential application of this reaction in functional modification and mild cleavage in solid-phase peptide synthesis. Thirteen peptide derivatives modified by trans-cyclooctene (TCO) were designed and synthesized, which were reacted with tetrazine to release the peptides. The results showed that the release rates of peptide were 90.0% to 97.7% in one hour. The strategy has good compatibility with the functional side-groups and the length of peptides, which expands the applications scope of tetrazine bioorthogonal click-to-release reaction. At the same time, a novel bifunctional trans-cyclooctene molecule was designed and synthesized. The active peptide GIRLRG was modified by fluorophore on the solid-phase resin, and released through tetrazine click-to-release reaction under mild condition, providing a new strategy for the solid-phase modification and release strategy of the peptide.

tetrazine  /  trans-cyclooctene  /  bioorthogonal reaction  /  solid-phase peptidesynthesis  /  click-to-release reaction
Xiao-meng WANG, Jie LI, Guo-hua SHEN, Li-li PAN, Rong TIAN, Hong-bao SUN, Hao-xing WU. Tetrazine bioorthogonal click-to-release reaction for releasing peptides[J]. Acta Pharmaceutica Sinica, 2020 , 55 (7) : 1634 -1646 . DOI: 10.16438/j.0513-4870.2020-0139
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Article Info
doi: 10.16438/j.0513-4870.2020-0139
  • Receive Date：2020-02-20
  • Online Date：2026-01-21
  • Published：2020-07-12
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History
  • Received：2020-02-20
  • Revised：2020-03-03
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Affiliations
    1. Department of Nuclear Medicine, West China Hospital, Sichuan University, Chengdu 610041, China
    2. Huaxi MR Research Center, West China Hospital, Sichuan University, Chengdu 610041, China
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表12种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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