Citation: Zhao Zhehui, Wang Apeng, Zhang Xiaoxi, Yang Shuang, Luo Zhigang, Lei Pingsheng. Synthesis of novel 5-O-(6'-O-modified)-desosamine 14-membered ketolides[J]. Chinese Chemical Letters, ;2019, 30(2): 425-427. doi: 10.1016/j.cclet.2018.04.014 shu

Synthesis of novel 5-O-(6'-O-modified)-desosamine 14-membered ketolides

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China

zhaozh@imm.ac.cn

lei@imm.ac.cn

Received Date: 29 January 2018
Revised Date: 11 April 2018
Accepted Date: 12 April 2018
Available Online: 13 February 2018

Figures(4)

A new and facile procedure was developed to synthesize novel 5-O-(6'-O-modified)-desosamine 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Two trichloroacetimidate donors, with Lev or Ac substituent groups at the C-6 position, were synthesized to couple with the erythronolide. Several novel 5-O-(6'-O-modified)-desosamine 14-membered ketolides were obtained to verify the utility of the method.
- Ketolides,
- Desosamine,
- Glycosyolation,
- Modification
1. [1]
  (a) H. Takashima, Curr. Top. Med. Chem. 3 (2003) 991-999.
2. [2]
  (a) N. LeTourneau, P. Vimal, D. Klepacki, A. Mankin, A. Melman, Bioorg. Med. Chem. Lett. 22 (2012) 4575-4578.
3. [3]
  L.T. Phan, T. Jian, Z. Chen, et al., J. Med. Chem. 47(2004) 2965-2968. doi: 10.1021/jm034233n
4. [4]
  A. Romero, C.H. Liang, Y.H. Chiu, et al., Tetrahedron Lett. 46(2005) 1483-1487. doi: 10.1016/j.tetlet.2005.01.023
5. [5]
  C.H. Liang, S. Yao, Y.H. Chiu, et al., Bioorg. Med. Chem. Lett. 15(2005) 1307-1310. doi: 10.1016/j.bmcl.2005.01.027
6. [6]
  (a) X.Z. Chen, P. Xu, Y.P. Xu, et al., Bioorg. Med. Chem. Lett. 22(2012) 7402-7405.
7. [7]
  A.P. Wang, C. Liu, S. Yang, Z.H. Zhao, P.S. Lei, Tetrahedron 72(2016) 285-297. doi: 10.1016/j.tet.2015.11.029
8. [8]
  H. Arita, N. Ueda, Y. Matsushima, B Chem. Soc. JPN. 45(1972) 567-569. doi: 10.1246/bcsj.45.567
9. [9]
  T. Yoshisuke, N. Tomoko, K. Fumiyuki, K. Yukihiko, Heterocycle 44(1997) 427-433. doi: 10.3987/COM-96-S41
10. [10]
  W.L. Chen, C.F. Xia, J.H. Wang, et al., J. Org. Chem. 72(2007) 9914-9923. doi: 10.1021/jo701539k
11. [11]
  P.D. Alexander, N.B. Charles, A.J.F. Michael, S.B. John, Tetrahedron Lett. 42(2001) 117-119. doi: 10.1016/S0040-4039(00)01900-6
12. [12]
  J. Xue, J. Wang, Z. Guo, Org. Lett. 6(2004) 1365-1368. doi: 10.1021/ol0499046
13. [13]
  P.B. Alper, S.C. Hung, C.H. Wong, Tetrahedron Lett. 37(1996) 6029-6032. doi: 10.1016/0040-4039(96)01307-X
14. [14]
  K. Rakesh, I.W. Leonard, E.K. Edward, J. Med. Chem. 36(1993) 2470-2474. doi: 10.1021/jm00069a004
15. [15]
  B. Luisa, N. Daniele, S. Corrado, S. Piero, J. Org. Chem. 64(1996) 7836-7841.
16. [16]
  E.F.V. Scriven, K. Turnbull, Chem. Rev. 88(1988) 298-360.
17. [17]
  B. Lusia, L. Rino, M. Matteo, et al., Tetrahedron 58(2002) 3485-3492. doi: 10.1016/S0040-4020(02)00302-2
18. [18]
  A. Shazia, D.V. Natasha, E.R. Joseph, R.J.P. David, Tetrahedron 69(2013) 816-825.
19. [19]
  J. Zhang, Y. Sun, X. Zhang, C. Li, H. Guan, Carbohydr. Res. 381(2013) 74-82. doi: 10.1016/j.carres.2013.08.010
20. [20]
  D. Mercedes, D.M. Julio, J. Org. Chem. 64(1999) 4798-4810. doi: 10.1021/jo9901438
1. [1]
  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
2. [2]
  Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
3. [3]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
4. [4]
  Wenbi Wu , Yinchu Dong , Haofan Liu , Xuebing Jiang , Li Li , Yi Zhang , Maling Gou . Modification of plasma protein for bioprinting via photopolymerization. Chinese Chemical Letters, 2024, 35(8): 109260-. doi: 10.1016/j.cclet.2023.109260
5. [5]
  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
6. [6]
  Fangling Cui , Zongjie Hu , Jiayu Huang , Xiaoju Li , Ruihu Wang . MXene-based materials for separator modification of lithium-sulfur batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100337-100337. doi: 10.1016/j.cjsc.2024.100337
7. [7]
  Chenghao Ge , Peng Wang , Pei Yuan , Tai Wu , Rongjun Zhao , Rong Huang , Lin Xie , Yong Hua . Tuning hot carrier transfer dynamics by perovskite surface modification. Chinese Chemical Letters, 2024, 35(10): 109352-. doi: 10.1016/j.cclet.2023.109352
8. [8]
  Yue Pan , Wenping Si , Yahao Li , Haotian Tan , Ji Liang , Feng Hou . Promoting exciton dissociation by metal ion modification in polymeric carbon nitride for photocatalysis. Chinese Chemical Letters, 2024, 35(12): 109877-. doi: 10.1016/j.cclet.2024.109877
9. [9]
  Yue Wang , Caixia Xu , Xingtao Tian , Siyu Wang , Yan Zhao . Challenges and Modification Strategies of High-Voltage Cathode Materials for Li-ion Batteries. Chinese Journal of Structural Chemistry, 2023, 42(10): 100167-100167. doi: 10.1016/j.cjsc.2023.100167
10. [10]
  Shu-Ran Xu , Fang-Xing Xiao . Metal halide perovskites quantum dots: Synthesis, and modification strategies for solar CO2 conversion. Chinese Journal of Structural Chemistry, 2023, 42(12): 100173-100173. doi: 10.1016/j.cjsc.2023.100173
11. [11]
  Fengyu Zhang , Yali Liang , Zhangran Ye , Lei Deng , Yunna Guo , Ping Qiu , Peng Jia , Qiaobao Zhang , Liqiang Zhang . Enhanced electrochemical performance of nanoscale single crystal NMC811 modification by coating LiNbO₃. Chinese Chemical Letters, 2024, 35(5): 108655-. doi: 10.1016/j.cclet.2023.108655
12. [12]
  Huan Yao , Jian Qin , Yan-Fang Wang , Song-Meng Wang , Liu-Huan Yi , Shi-Yao Li , Fangfang Du , Liu-Pan Yang , Li-Li Wang . Ultra-highly selective recognition of nucleosides over nucleotides by rational modification of tetralactam macrocycle and its application in enzyme assay. Chinese Chemical Letters, 2024, 35(6): 109154-. doi: 10.1016/j.cclet.2023.109154
13. [13]
  Xin Zhang , Junyu Chen , Xiang Pei , Linxin Yang , Liang Wang , Luona Chen , Guangmei Yang , Xibo Pei , Qianbing Wan , Jian Wang . Drug-loading ZIF-8 for modification of microporous bone scaffold to promote vascularized bone regeneration. Chinese Chemical Letters, 2024, 35(6): 108889-. doi: 10.1016/j.cclet.2023.108889
14. [14]
  Zeyu XU , Tongzhou LU , Haibo SHAO , Jianming WANG . Preparation and electrochemical lithium storage performance of porous silicon microsphere composite with metal modification and carbon coating. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1995-2008. doi: 10.11862/CJIC.20240164
15. [15]
  Shaoming Dong , Yiming Niu , Yinghui Pu , Yongzhao Wang , Bingsen Zhang . Subsurface carbon modification of Ni-Ga for improved selectivity in acetylene hydrogenation reaction. Chinese Chemical Letters, 2024, 35(12): 109525-. doi: 10.1016/j.cclet.2024.109525
16. [16]
  Junqing Wu , Yiyang Zhang , Qingqing Hong , Hui Yang , Lifeng Zhang , Ming Zhang , Lei Yu . Organometallic modification of silica with europium endowing the fluorescence properties: The key technique for numerical quality monitoring. Chinese Chemical Letters, 2025, 36(4): 110165-. doi: 10.1016/j.cclet.2024.110165
17. [17]
  Yang LIU , Lijun WANG , Hongyu WANG , Zhidong CHEN , Lin SUN . Surface and interface modification of porous silicon anodes in lithium-ion batteries by the introduction of heterogeneous atoms and hybrid encapsulation. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 773-785. doi: 10.11862/CJIC.20250015
18. [18]
  Jian Li , Jinjin Chen , Qi-Long Hu , Zhen Wang , Xiao-Feng Xiong . Recent progress of chemical methods for lysine site-selective modification of peptides and proteins. Chinese Chemical Letters, 2025, 36(5): 110126-. doi: 10.1016/j.cclet.2024.110126
19. [19]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
20. [20]
  Yunfa Dong , Shijie Zhong , Yuhui He , Zhezhi Liu , Shengyu Zhou , Qun Li , Yashuai Pang , Haodong Xie , Yuanpeng Ji , Yuanpeng Liu , Jiecai Han , Weidong He . Modification strategies for non-aqueous, highly proton-conductive benzimidazole-based high-temperature proton exchange membranes. Chinese Chemical Letters, 2024, 35(4): 109261-. doi: 10.1016/j.cclet.2023.109261

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1215)
HTML views(78)

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