DIC/Oxyma Based Efficient Synthesis and Activity Evaluation of Spider Peptide Toxin GsMTx4

doi:10.6023/cjoc202109003

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 498-506.DOI: 10.6023/cjoc202109003 Previous Articles Next Articles

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基于DIC/Oxyma的蜘蛛毒素多肽GsMTx4的高效合成及活性评价

马艳楠^a, 刘雅妮^a, 王金艳^a, 陈西同^a, 尹昊^a, 迟巧娜^b, 贾世玺^b, 杜姗姗^b^,^c, 齐昀坤^a^,^c^,^*(), 王克威^a^,^c

a 青岛大学药学院山东青岛 266073
b 青岛科技大学化工学院山东青岛 266042
c 青岛大学创新药物研究院山东青岛 266021

收稿日期:2021-09-01 修回日期:2021-09-21 发布日期:2022-02-24
通讯作者: 齐昀坤
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(21807063); 国家自然科学基金(82003647); 国家自然科学基金(22177058); 中国博士后科学基金(2019M652307); 中国博士后科学基金(2020T130332); 山东省自然科学基金(ZR2019BH045); 山东省自然科学基金(ZR2020QH100)

DIC/Oxyma Based Efficient Synthesis and Activity Evaluation of Spider Peptide Toxin GsMTx4

Yannan Ma^a, Ya'ni Liu^a, Jinyan Wang^a, Xitong Chen^a, Hao Yin^a, Qiaona Chi^b, Shixi Jia^b, Shanshan Du^b^,^c, Yunkun Qi^a^,^c(), Kewei Wang^a^,^c

a School of Pharmacy, Qingdao University, Qingdao, Shandong 266073
b College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042
c Institute of Innovative Drugs, Qingdao University, Qingdao, Shandong 266021

Received:2021-09-01 Revised:2021-09-21 Published:2022-02-24
Contact: Yunkun Qi
About author:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21807063); National Natural Science Foundation of China(82003647); National Natural Science Foundation of China(22177058); China Postdoctoral Science Foundation(2019M652307); China Postdoctoral Science Foundation(2020T130332); Natural Science Foundation of Shandong Province(ZR2019BH045); Natural Science Foundation of Shandong Province(ZR2020QH100)

Coupling reagents mediate the formation of amide bonds and play a key role in solid phase peptide synthesis. The novel N,N-diisopropylcarbodiimide (DIC)/ethyl cyanoglyoxylate-2-oxime (Oxyma) condensation system has the advantages of low cost, operational safety, higher coupling efficiency and lower rate of racemization. The DIC/Oxyma condensation system has been widely used in manual and automated synthesis of peptides. However, the ideal reaction ratio in DIC/Oxyma condensation system at mild reaction temperature remains to be further investigated. GsMTx4 is a cysteine rich peptide toxin identified from the venom of Grammostola spatulata spider, which consists of 34 amino acid residues and three pairs of disulfide bonds. GsMTx4 is the only inhibitor specifically targeting piezo channel, which is a multifunctional mechanically sensitive cation channel and associated with a variety of hereditary diseases. Herein, the synthetic efficiencies of different reaction ratios of DIC and Oxyma at moderate reaction temperature were systematically evaluated. The efficiency and robustness of DIC/Oxyma condensation system were validated by the rapid manual synthesis of linear GsMTx4. The one-step oxidative folding strategy was applied for the construction of three pairs of disulfide bridges, affording the active GsMTx4. The circular dichroism and patch-clamp electrophysiology tests were conducted to evaluate the structure and activity of synthetic GsMTx4. In summary, a fast, robust and safe synthetic method based on DIC/Oxyma is established, which is particularly useful for the manual synthesis of peptides.

Key words: DIC, Oxyma, solid phase peptide synthesis, disulfide bond, oxidative folding, GsMTx4, peptide toxin

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Yannan Ma, Ya'ni Liu, Jinyan Wang, Xitong Chen, Hao Yin, Qiaona Chi, Shixi Jia, Shanshan Du, Yunkun Qi, Kewei Wang. DIC/Oxyma Based Efficient Synthesis and Activity Evaluation of Spider Peptide Toxin GsMTx4[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 498-506.

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Fig. & Tab. 10

Figure 1. Structures of HOAt, HOBt, DIC and Oxyma

Figure 2. Reaction mechanism of DIC/Oxyma condensation system

Figure 3. Amino acid sequence of spider toxin GsMTx4

Figure 4. Solid phase peptide synthesis and oxidative folding of GsMTx4

Linear peptide	Reaction molar ratio	Reaction temperature/℃	HPLC purity/%	Isolated yield/%	Yield/mg
GsMTx4-1	n(Aa)∶n(HCTU)∶n(DIEA)=4∶3.8∶8	28	51	18	37
GsMTx4-2	n(Aa)∶n(DIC)∶n(Oxyma)=4∶8∶4	50	46	16	33
GsMTx4-3	n(Aa)∶n(DIC)∶n(Oxyma)=4∶12∶4	50	41	14	29
GsMTx4-4	n(Aa)∶n(DIC)∶n(Oxyma)=4∶4∶8	50	37	12	25

Table 1. Synthetic strategy, HPLC (high performance liquid chromatography) purity and isolated yield of linear GsMTx4

Figure 5. Analytical RP-HPLC and ESI-MS spectra of crude peptides and purified peptides of (A) GsMTx4-1, (B) GsMTx4-2, (C) GsMTx4-3 and (D) GsMTx4-4 RP-HPLC conditions: a linear gradient of 5%~60% buffer B [0.08%~0.1% TFA (trifluoroacetic acid) in CH3CN] in buffer A (0.1% TFA in water) over 30 min (5% for 2 min, then 5%~60% for 30 min) on a Vydac C18 column, λ=214 nm

Figure 6. Analytical RP-HPLC and ESI-MS spectra of one-step oxidative folding process of peptides of (A) GsMTx4-1, (B) GsMTx4-2, (C) GsMTx4-3, and (D) GsMTx4-4 (A) (a)~(b) The RP-HPLC spectra of the folding solution for GsMTx4-1 at 0 min and 12 h, (c) The RP-HPLC and ESI-MS spectra of purified GsMTx4-5. (B) (d)~(e) The RP-HPLC spectra of the folding solution for GsMTx4-2 at 0 min and 12 h, (f) The RP-HPLC and ESI-MS spectra of purified GsMTx4-6. (C) (g)~(h) The RP-HPLC spectra of the folding solution for GsMTx4-3 at 0 min and 12 h, (i) The RP-HPLC and ESI-MS spectra of purified GsMTx4-7. (D) (j)~(k) The RP-HPLC spectra of the folding solution for GsMTx4-4 at 0 min and 12 h, (l) The RP-HPLC and ESI-MS spectra of purified GsMTx4-8. RP-HPLC conditions: a linear gradient of 5%~60% buffer B in buffer A over 30 min (5% for 2 min, then 5%~60% for 30 min) on a Vydac C18 column, λ=214 nm

Linear peptide	Folding product	HPLC purity/%	Isolated yield/%	Yield/mg	Calculated mass	Observed mass
GsMTx4-1	GsMTx4-5	51	28	8.4	4095.90	4094.93
GsMTx4-2	GsMTx4-6	45	24	7.2	4095.90	4094.93
GsMTx4-3	GsMTx4-7	46	25	7.5	4095.90	4095.32
GsMTx4-4	GsMTx4-8	45	25	7.5	4095.90	4094.94

Table 2. HPLC purity, isolated yield and ESI-MS data of one-step oxidative folding strategy for GsMTx4

Figure 7. (A) Analytical RP-HPLC and high resolution ESI-MS spectra of GsMTx4-5, GsMTx4-6, GsMTx4-7, GsMTx4-8 and GsMTx4-9 co-injections, and (B) circular dichroism spectra of GsMTx4-1, GsMTx4-5, GsMTx4-6, GsMTx4-7, GsMTx4-8 and GsMTx4-9

Figure 8. Inhibitory effect of peptides GsMTx4-5, GsMTx4-6, GsMTx4-7, GsMTx4-8, GsMTx4-9 and GsMTx4-1 on Piezo1 channel (A)~(F) The typical current traces (Left) and time courses (Right) of Piezo1 currents inhibited by GsMTx4-9, GsMTx4-5, GsMTx4-6, GsMTx4-7, GsMTx4-8 and GsMTx4-1. (G) The normalized inhibition rate of Piezo1 currents by GsMTx4-5, GsMTx4-6, GsMTx4-7, GsMTx4-8, GsMTx4-9 and GsMTx4-1. n=4~6, each data point is represented as mean±SEM, ***p<0.001 (compared with the GsMTx4-1 group), ns: no significance

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基于DIC/Oxyma的蜘蛛毒素多肽GsMTx4的高效合成及活性评价

DIC/Oxyma Based Efficient Synthesis and Activity Evaluation of Spider Peptide Toxin GsMTx4

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