人血管加压素糖基化衍生物的合成

doi:10.5246/jcps.2017.09.072

中国药学(英文版) ›› 2017, Vol. 26 ›› Issue (9): 642-649.DOI: 10.5246/jcps.2017.09.072

人血管加压素糖基化衍生物的合成

李红星, 袁宁, 董甦伟^*

北京大学医学部药学院天然药物及仿生药物国家重点实验室; 化学生物学系, 北京 100191

收稿日期:2017-06-07 修回日期:2017-08-02 出版日期:2017-09-30 发布日期:2017-09-04
通讯作者: Tel.: +86-010-82805931, E-mail: dongs@bjmu.edu.cn
基金资助:
Peking University Health Science Center (BMU20130354), State Key Laboratory of Natural and Biomimetic Drugs, and the National Recruitment Program of Global Youth Experts (1000 Plan).

The glycosylation-oriented engineering of human vasopressin

Hongxing Li, Ning Yuan, Suwei Dong^*

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2017-06-07 Revised:2017-08-02 Online:2017-09-30 Published:2017-09-04
Contact: Tel.: +86-010-82805931, E-mail: dongs@bjmu.edu.cn
Supported by:
Peking University Health Science Center (BMU20130354), State Key Laboratory of Natural and Biomimetic Drugs, and the National Recruitment Program of Global Youth Experts (1000 Plan).

摘要/Abstract

摘要：

本文建立了以糖-氨基酸缀合物作为固相合成模块、快速制备人血管加压素糖基化衍生物的策略, 为高效合成其它结构新颖的糖基化环肽及衍生物提供了一个解决方案。

关键词: 血管加压素, 糖基化, 环肽

Abstract:

A glycosylamino acid “cassette”-based synthetic route has been developed for the preparation of vasopressin analogues with glycosylation. This efficient protocol may be utilized in the synthesis of other novel cyclic glycopeptide structures and derivatives.

Key words: Vasopressin, Glycosylation, Cyclic glycopeptide

中图分类号:

R916

Supporting:

1. Peptide 19

Figure S1. HPLC trace and ESI-MS data of peptide 19. Linear gradient: 10%–30% solvent B over 30 min, Agilent C₁₈ column, t_R = 19 min; Calcd for C₄₆H₆₇N₁₅O₁₂S₂: 1086.26 Da (average isotopes), [M+1H]⁺ m/z = 1087.26, [M+2H]²⁺ m/z = 544.13; observed [M+H]⁺ m/z = 1086.43, [M+2H]²⁺ m/z = 544.02.

2. Glycopeptide 20

Figure S2. HPLC trace and ESI-MS data of peptide 20. Linear gradient: 10%–30% solvent B over 30 min, Agilent C₁₈ column, t_R = 19.3 min; Calcd for C₅₈H₈₇N₁₇O₁₉S₂: 1390.55 Da (average isotopes), [M+1H]⁺ m/z = 1391.55, [M+2H]²⁺ m/z = 696.28; observed: [M+1H]⁺ m/z = 1390.55, 1187.47^*, [M+2H]²⁺ m/z = 696.20, 594.61^*. ^*Signals denote the GlcNAc-cleaved species during ionization in mass spectrometry.

3. Glycopeptide 21

Figure S3. HPLC trace and ESI-MS data of peptide 21. Linear gradient: 10%–30% solvent B over 30 min, Agilent C₁₈ column, t_R = 17.9 min; Calcd for C₅₄H₈₀N₁₆O₁₇S₂: 1289.45 Da (average isotopes), [M+1H]⁺ m/z = 1290.45, [M+2H]²⁺ m/z = 645.72; observed: [M+1H]⁺ m/z = 1289.55, [M+2H]²⁺ m/z = 645.52. ^#Peak denotes the oxidized species (3) after storage for several days.

4. Glycopeptide 22

Figure S4. HPLC trace and ESI-MS data of peptide 22. Linear gradient: 10%–30% solvent B over 30 min, Agilent C₁₈ column, t_R = 17.5 min; Calcd for C₅₄H₈₀N₁₆O₁₇S₂: 1289.45 Da (average isotopes), [M+1H]⁺ m/z = 1290.45, [M+2H]²⁺ m/z = 645.72; observed: [M+1H]⁺ m/z = 1289.61, [M+2H]²⁺ m/z = 645.58.

5. Cyclopeptide 1

Figure S5. HPLC trace and ESI-MS data of peptide 1. Linear gradient: 10%–30% solvent B over 30 min, Agilent C₁₈ column, t_R = 19.2 min; Calcd for C₄₆H₆₅N₁₅O₁₂S₂: 1084.24 Da (average isotopes), [M+1H]⁺ m/z = 1085.24, [M+2H]²⁺ m/z = 543.12; observed: [M+1H]⁺ m/z = 1084.41, [M+2H]²⁺ m/z = 543.08.

6. Glycopeptide 2

Figure S6. HPLC trace and ESI-MS data of peptide 2. Linear gradient: 10%–30% solvent B over 30 min, Agilent C₁₈ column, t_R = 18.7 min; Calcd for C₅₈H₈₅N₁₇O₁₉S₂: 1388.54 Da (average isotopes), [M+1H]⁺ m/z = 1389.54, [M+2H]²⁺ m/z = 695.27; observed: m/z = 1388.69, 1185.59^*, [M+2H]²⁺ m/z = 695.08, 593.51^*. ^*Signals denote the GlcNAc-cleaved species during ionization in mass spectrometry.

7. Glycopeptide 3

Figure S7. HPLC trace and ESI-MS data of peptide 3. Linear gradient: 10%–30% solvent B over 30 min, Agilent C18 column, t_R = 16.8 min; Calcd for C₅₄H₇₈N₁₆O₁₇S₂: 1287.43 Da (average isotopes), [M+1H]⁺ m/z = 1288.43, [M+2H]²⁺ m/z = 644.72; observed: [M+1H]⁺ m/z = 1287.50, [M+2H]²⁺ m/z = 644.59.

8. Glycopeptide 4

Figure S8. HPLC trace and ESI-MS data of peptide 4. Linear gradient: 10%–30% solvent B over 30 min, Agilent C₁₈ column, t_R = 17.2 min; Calcd for C₅₄H₇₈N₁₆O₁₇S₂: 1287.43 Da (average isotopes), [M+1H]⁺ m/z = 1288.43, [M+2H]²⁺ m/z = 644.72; observed: [M+1H]⁺ m/z = 1287.50, [M+2H]²⁺ m/z = 644.53.

李红星, 袁宁, 董甦伟. 人血管加压素糖基化衍生物的合成[J]. 中国药学(英文版), 2017, 26(9): 642-649.

Hongxing Li, Ning Yuan, Suwei Dong. The glycosylation-oriented engineering of human vasopressin[J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(9): 642-649.

参考文献

[1] Kounin, G.; Bashir, Q. Surg. Neurol. 2000, 53, 508–510.

[2] Treschan, T.A.; Peters, J. J. Am. Soc. Anesthesiol. 2006, 105, 599–612.

[3] Holt, N.F.; Haspel, K.L. J. Cardiothorac. Vasc. Anesth. 2010, 24, 330–347.

[4] Robinson, A.G. N. Engl. J. Med. 1976, 294, 507–511.

[5] Richardson, D.W. Ann. Intern. Med. 1985, 103, 228.

[6] Pesaturo, A.B.; Jennings, H.R.; Voils, S.A. Ann. Pharmacother. 2006, 40, 2170–2177.

[7] Uriz, J.; Ginès, P.; Cárdenas, A.; Sort, P.; Jiménez, W.; Salmerón, J.M.; Bataller, R.; Mas, A.; Navasa, M.; Arroyo, V.; Rodés, J. J. Hepatol. 2000, 33, 43–48.

[8] Elliott, S.; Lorenzini, T.; Asher, S.; Aoki, K.; Brankow, D.; Buck, L.; Busse, L.; Chang, D.; Fuller, J.; Grant, J.; Hernday, N.; Hokum, M.; Hu, S.; Knudten, A.; Levin, N.; Komorowski, R.; Martin, F.; Navarro, R.; Osslund, T.; Rogers, G.; Rogers, N.; Trail, G.; Egrie, J. Nat. Biotechnol. 2003, 21, 414–421.

[9] Walsh, G.; Jefferis, R. Nat. Biotechnol. 2006, 24, 1241–1252.

[10] Moradi, S.V.; Hussein, W.M.; Varamini, P.; Simerska, P.; Toth, I. Chem. Sci. 2016, 7, 2492–2500.

[11] Hu, H.; Xue, J.; Swarts, B. M.; Wang, Q.; Wu, Q.; Guo, Z. J. Med. Chem. 2009, 52, 2052–2059.

[12] Zou, Y.; Zhao, Q.; Zhang, C.; Wang, L.; Li, W.; Li, X.; Wu, Q.; Hu, H. J. Pept. Sci. 2015, 21, 586–592.

[13] Zhao, Q.; Zou, Y.; Guo, J.; Yu, S.; Chai, X.; Hu, H.; Wu, Q. Tetrahedron. 2014, 70, 7780–7787.

[14] Kihlberg, J.; Aahman, J.; Walse, B.; Drakenberg, T.; Nilsson, A.; Soederberg-Ahlm, C.; Bengtsson, B.; Olsson, H. J. Med. Chem. 1995, 38, 161–169.

[15] Suzuki, K.; Susaki, H.; Okuno, S.; Yamada, H.; Watanabe, H.K.; Sugiyama, Y. J. Pharmacol. Exp. Ther. 1999, 288, 888–897.

[16] Susaki, H.; Suzuki, K.; Yamada, H.; Okuno, S.; Watanabe, H.K. Biol. Pharm. Bull. 1999, 22, 1094–1098.

[17] Peter-Katalinić, J. Methods. Enzymol. 2005, 139–171.

[18] Schwarz, F.; Aebi, M. Curr. Opin. Struct. Biol. 2011, 21, 576–582.

[19] Lannoo, N.; Van Damme, E.J.M. Plant Sci. 2015, 239, 67–83.

[20] Dullenkopf, W.; Castro-Palomino, J.C.; Manzoni, L.; Schmidt, R.R. Carbohydr. Res. 1996, 296, 135–147.

[21] Graham, M.E.; Stone, R.S.; Robinson, P.J.; Payne, R.J. Org. Biomol. Chem. 2012, 10, 2545.

[22] Premdjee, B.; Adams, A. L.; Macmillan, D. Bioorg. Med. Chem. Lett. 2011, 21, 4973–4975.

[23] Cao, Z.; Qu, Y.; Zhou, J.; Liu, W.; Yao, G. J. Carbohydr. Chem. 2015, 34, 28–40.

[24] Zhang, Y.; Muthana, S. M.; Farnsworth, D.; Ludek, O.; Adams, K.; Barchi, J.J.; Gildersleeve, J.C. J. Am. Chem. Soc. 2012, 134, 6316–6325.
[25] Kajihara, Y.; Tanabe, Y.; Sasaoka, S.; Okamoto, R. Chem. Eur. J. 2012, 18, 5944–5953.

人血管加压素糖基化衍生物的合成

The glycosylation-oriented engineering of human vasopressin

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