Citation: Ye Huang, Wen-Hua Feng. N,O-Bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) as coupling agents for dipeptide synthesis[J]. Chinese Chemical Letters, ;2016, 27(03): 357-360. doi: 10.1016/j.cclet.2015.11.012 shu

N,O-Bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) as coupling agents for dipeptide synthesis

Ye Huang ,
Wen-Hua Feng ^,

1.
Department of New Drug Research and Development, Institute of Materia Medica & Peking Union Medical College, Chinese Academy of Medical Sciences, Beijing 100050, China

Corresponding author: Wen-Hua Feng,
Received Date: 29 September 2015
Available Online: 26 October 2015
Fund Project:

A method using N,O-bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) as coupling agents for dipeptide synthesis is descried. The coupling reaction between N-hydroxysuccinimide (NHS) esters and amines could be performed under mild conditions with N,O-bis(trimethylsilyl)acetamide (BSA) as coupling reagent and no additional acid/base is required. All byproducts and excessive reactants are water soluble or hydrolysable and easy to eliminate through water-washing at the purification stage. Moreover, all the reactants are inexpensive and widely used in conventional drug production.
- Dipeptide synthesis,
- Solution-phase,
- N,O-Bis(trimethylsilyl)acetamide,
- N-Hydroxysuccinimide ester,
- Water washing
1. [1]
  [1] V. du Vigneaud, C. Ressler, J.M. Swan, et al., The synthesis of an octapeptide amide with the hormonal activity of oxytocin, J. Am. Chem. Soc. 75(1953) 4879-4880.
2. [2]
  [2] C.M. Cloutheir, J.N. Pelleteir, Expanding the organic toolbox:a guide to integrating biocatalysis in synthesis, Chem. Soc. Rev. 41(2012) 1585-1605.
3. [3]
  [3] B.L. Bray, Large-scale manufacture of peptide therapeutics by chemical synthesis, Nat. Rev. Drug Discov. 2(2003) 587-593.
4. [4]
  [4] S. Maher, B. Ryan, A. Duffy, et al., Formulation strategies to improve oral peptide delivery, Pharm. Pat. Anal. 3(2014) 313-336.
5. [5]
  [5] (a) T.R. Pearce, K. Shroff, E. Kokkoli, Peptide targeted lipid nanoparticles for anticancer drug delivery, Adv. Mater. 24(2014) 3803-3822;
6. [6]
  (b) L.T. Eliassen, G. Berge, B. Sveinbjornsson, et al., Evidence for a direct antitumor mechanism of action of bovine lactoferricin, Anticancer Res. 22(2002) 2703-2710.
7. [7]
  [6] (a) L.L. Baggio, Q. Huang, T.J. Brown, et al., A recombinant human glucagon-like peptide (GLP)-1-albumin protein (Albugon) mimics peptidergic activation of GLP-1 receptor-dependent pathways coupled with satiety, gastrointestinal motility, and glucose homeostasis, Diabetes 53(2004) 2492-2500;
8. [8]
  (b) Q. Xiao, J. Giguere, M. Parisien, et al., Biological activities of glucagon-like peptide-1 analogues in vitro and in vivo, Biochemistry 40(2001) 2860-2869.
9. [9]
  [7] C.D. Fiell, J.A. Hiss, R.E.W. Hancock, et al., Designing antimicrobial peptides:form follows function, Nat. Rev. Drug Discov. 11(2012) 37-51.
10. [10]
  [8] S. Matsunaga, N. Fusetani, K. Hashimoto, et al.,F. Theonellamide, A novel antifungal bicyclic peptide from a marine sponge Theonella sp, J. Am. Chem. Soc. 111(1989) 2582-2588.
11. [11]
  [9] (a) N. Kaur, X. Lu, M.C. Gerhengorn, et al., Thyrotropin-releasing hormone (TRH) analogues that exhibit selectivity to TRH receptor subtype 2, J. Med. Chem. 48(2005) 6162-6165;
12. [12]
  (b) J. Rivier, W. Vale, M. Monahan, et al., Synthetic thyrotropin-releasing factor analogs. 3. Effect of replacement or modification of histidine residue on biological activity, J. Med. Chem. 15(1972) 479-482.
13. [13]
  [10] R.B. Merrifield, Solid phase peptide synthesis. (Ⅰ). The synthesis of a tetrapeptide, J. Am. Chem. Soc. 85(1963) 2149-2154.
14. [14]
  [11] T. Bruckdorfer, O. Marder, F. Albericio, From production of peptides in milligram amounts for research to multi-tons quantities for drugs of the future, Curr. Pharm. Biotechnol. 5(2004) 29-43.
15. [15]
  [12] (a) E. Bayer, M. Mutter, Liquid phase synthesis of peptides, Nature 237(1972) 512-513;
16. [16]
  (b) J. Wu, G. An, S. Lin, et al., Solution-phase-peptide synthesis via the groupassisted purification (GAP) chemistry without using chromatography and recrystallization, Chem. Commun. 50(2014) 1259-1261;
17. [17]
  (c) G. Tana, S. Kitada, S. Fujita, et al., A practical solution-phase synthesis of an antagonistic peptide of TNF-abased on hydrophobic tag strategy, Chem. Commun. 46(2010) 8219-8221;
18. [18]
  (d) M. Mizuno, K. Goto, T. Miura, et al., A novel peptide synthesis using fluorous chemistry, Chem. Commun. 8(2003) 972-973;
19. [19]
  (e) D. Takahashi, T. Yano, T. Fukui, Novel diphenylmethyl-derived amide protecting group for efficient liquid-phase peptide synthesis:AJ(Ⅰ)PHASE, Org. Lett. 14(2014) 4514-4517;
20. [20]
  (f) N. Naganna, N. Madhavan, Soluble non-cross-linked poly(norbornene) supports for peptide synthesis with minimal reagents, J. Org. Chem. 79(2014) 11549-11557;
21. [21]
  (g) Y. Fujita, S. Fujita, Y. Okada, et al., Soluble tag-assisted peptide head-to-tail cyclization:total synthesis of mahafacyclin B, Org. Lett. 15(2013) 1155-1157.
22. [22]
  [13] ChristianA.G.N. Montalbetti, V. Falque, Amide bond formation and peptide coupling, Tetrahedron 61(2005) 10827-10852.
23. [23]
  [14] M. Mikolajczyk, P. Kielbasinski, Recent developments in the carbodiimide chemistry, Tetrahedron 37(1981) 233-284.
24. [24]
  [15] (a) J.F. Klebe, in:E.C. Taylor (Ed.), Advances in Organic Chemistry, vol. 8, John Wiley and Sons, (Ⅰ)nc, New York, NY, 1972, p. 124;
25. [25]
  (b) B. Rigo, C. Lespagnol, M. Pauly, Studies on pyrrolidinones. Synthesis of Nacylpyroglutamic esters with bactericide and fungicide properties, J. Heterocycl. Chem. 25(1988) 49-57;
26. [26]
  (c) C. Bolm, A. Kasyan, K. Drauz, et al., α-Trialkylsilyl-substituted α-amino acid, Angew. Chem. (Ⅰ)nt. Ed. Engl. 39(2000) 2288-2290;
27. [27]
  (d) A.B. Ouryupina, V.Y. Komissarova, P.V. Petrovskiia, et al., Synthesis of n-phosphorylated aminoacids, Phosphorus Sulfur Silicon Relat. Elem. 103(1995) 215-224;
28. [28]
  (e) H. Fu, Z.L. Li, Y.F. Zhao, et al., Oligomerization of n,o-bis(trimethylsilyl)-α-amino acids into peptides mediated by o-phenylene ohosphorochloridate, J. Am. Chem. Soc. 121(1999) 291-295;
29. [29]
  (f) R.P. Singh, T. Umemoto, 4-Fluoropyrrolidine-2-carbonyl fluorides:useful synthons and their facile preparation with 4-tertbutyl-2,6-dimethylphenylsulfur trifluoride, J. Org. Chem. 76(2011) 3113-3121.
1. [1]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
2. [2]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
3. [3]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
4. [4]
  Shuangying Li , Qingxiang Zhou , Zhi Li , Menghua Liu , Yanhui Li . Sensitive measurement of silver ions in environmental water samples integrating magnetic ion-imprinted solid phase extraction and carbon dot fluorescent sensor. Chinese Chemical Letters, 2024, 35(5): 108693-. doi: 10.1016/j.cclet.2023.108693
5. [5]
  Shengyu Zhao , Qinhao Shi , Wuliang Feng , Yang Liu , Xinxin Yang , Xingli Zou , Xionggang Lu , Yufeng Zhao . Suppression of multistep phase transitions of O3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(5): 108606-. doi: 10.1016/j.cclet.2023.108606
6. [6]
  Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2023.100332
7. [7]
  Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
8. [8]
  Kunyao Peng , Xianbin Wang , Xingbin Yan . Converting LiNO₃ additive to single nitrogenous component Li₂N₂O₂ SEI layer on Li metal anode in carbonate-based electrolyte. Chinese Chemical Letters, 2024, 35(9): 109274-. doi: 10.1016/j.cclet.2023.109274
9. [9]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
10. [10]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
11. [11]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
12. [12]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
13. [13]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
14. [14]
  Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb₂O₆/Nitrogen-Enriched C₃N₅ S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016
15. [15]
  Lijun Mao , Shuo Li , Xin Zhang , Zhan-Ting Li , Da Ma . Cucurbit[n]uril-based nanostructure construction and modification. Chinese Chemical Letters, 2024, 35(8): 109363-. doi: 10.1016/j.cclet.2023.109363
16. [16]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
17. [17]
  Yun-Xin Huang , Lin-Qian Yu , Ke-Yu Chen , Hao Wang , Shou-Yan Zhao , Bao-Cheng Huang , Ren-Cun Jin . Biochar with self-doped N to activate peroxymonosulfate for bisphenol-A degradation via electron transfer mechanism: The active edge graphitic N site. Chinese Chemical Letters, 2024, 35(9): 109437-. doi: 10.1016/j.cclet.2023.109437
18. [18]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
19. [19]
  Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
20. [20]
  Kun Tang , Yu-Wu Zhong . Water reduction by an organic single-chromophore photocatalyst. Chinese Journal of Structural Chemistry, 2024, 43(8): 100376-100376. doi: 10.1016/j.cjsc.2024.100376

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(688)
HTML views(49)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142