中文
Earlier issues
Announcement
More
Progress in Chemistry 2006, Vol. 18 Issue (0203): 262-269 Previous Articles   Next Articles

• Review •

New Development of Coupling Reagents for Hindered Peptide

Liqin Jiang;Ligong Chen*   

  1. Institute of Pharmaceuticals & Biotechnology, Tianjin University, Tianjin 300072, China
  • Received: Revised: Online: Published:
  • Contact:

    Ligong Chen

PDF ( 2797 ) Cited
Export

EndNote

Ris

BibTeX

Recent development of coupling reagents and methods for hindered peptide containing N-alkylated or Cα，Cα-disubstituted amino acid residues is reviewed. The advantages and disadvantages of these coupling reagents and methods are discussed.
Key words: coupling reagents, N-alkyl amino acids, Cα, Cα-disubstituted amino acids

CLC Number: 

[ 1 ] Slomczynska U , Beusen D D , Zabrocki J , et al . J . Am. Chem.Soc. , 1992 , 114 : 4095 —4106
[ 2 ] Fusetani N , Matsunaga S. Chem. Rev. , 1993 , 93 : 1793 —1806
[ 3 ] McDermott J R , Benoiton N L. Can. J . Chem. , 1973 , 51 :2555 —2561
[ 4 ] Sammes P G, Weller D J . Synthesis , 1995 , 1205 —1222
[ 5 ] Humphrey J M, Chamberlin R A. Chem. Rev. , 1997 , 97 :2243 —2266
[ 6 ] Li P , Xu J C. J . Pept . Res. , 2000 , 58 (2 ) : 129 —139
[ 7 ] Wischnat R , Rudolph J , Hanke R , Kaese R , May A , Theis H ,Zuther U. Tetrahedron Lett . , 2003 , 44 : 4393 —4394
[ 8 ] Li P , Xu J C. Tetrahedron Lett . , 1999 , 40 : 8301 —8304
[ 9 ] Li P , Xu J C. Tetrahedron , 2000 , 56 : 8119 —8131
[10] Li P , Xu J C. J . Org. Chem. , 2000 , 65 : 2951 —2958
[11] Akaji K, Kuriyama N , Kiso Y. J . Org. Chem. , 1996 , 61 :3350 —3357
[12] Akaji K, Kuriyama N , Kiso Y. Tetrahedron Lett . , 1994 , 35 :3315 —3318
[13] Akaji K, Hayashi Y, Kiso Y, Kuriyama N. J . Org. Chem. ,1999 , 64 : 405 —411
[14] Li P , Xu J C. Tetrahedron , 2000 , 56 : 9949 —9955
[15] Carpino L A , Beyermann M, Wenschuh H , Bienert M. Acc.Chem. Res. , 1996 , 29 : 268 —274
[16] Falb E , Yechezkel T, Salitra Y, Gilon C. J . Pept . Res. , 1999 ,53 : 507 —517
[17] Falb E , Yechezkel T, Salitra Y, Palb E. WO 200 002 898-1 ,1999
[18] Thern B , Rudolph J , Jung G. Tetrahedron Lett . , 2002 , 43 :5013 —5016
[19] Angell Y M, Garcia-Echeverria C , Rich D H. Tetrahedron Lett . ,1994 , 35 (33) : 5981 —5984
[20] Angell Y M, Thomas T L , Flentke G R , Rich D H. J . Am.Chem. Soc. , 1995 , 117 : 7279 —7280
[21] Carpino L A , El-Faham A , Minor C A. J . Chem. Soc. , Chem.Commun. , 1994 , 201 —203
[22] Raman P , Stokes S S , Angell Y M, Flentke G R , Rich D H. J .Org. Chem. , 1998 , 63 : 5734 —5735
[23] Ko S Y, Wenger R M. Helv. Chim. Acta , 1997 , 80 : 695 —705
[24] Wijkmans J C H M, Blok F A A , van der Marel GA , van Boom J H , Bloemhoff W. Tetrahedron Lett . , 1995 , 36 , (26) : 4643 —4646
[25] Fang J B , Sanghi R , Kohn J , Goldman A S. Inorganica Chimica Acta. 2004 , 357 : 2415 —2426
[26] Nishiyama Y, Ishizuka S , Mori T, Kurita K. Chem. Pharm.Bull . , 1999 , 47 (4) : 576 —578
[27] Nishiyama Y, Ishizuka S , Mori T, Kurita K. Chem. Pharm.Bull . , 2000 , 48 (3) : 442 —444
[28] Nishiyama Y, Ishizuka S , Kurita K. Tetrahedron Lett . , 2001 ,42 : 8789 —8791
[29] Carpino L A , Sadat-Aalacc D , Chao H G, DeSelms R H. J . Am.Chem. Soc. , 1990 , 112 : 9651 —9652
[30] Wenshuh H , Beyermann M, E1-Faham A , Ghassemi S ,Carpino L A. J . Chem. Soc. , Chem. Commun. , 1995 , 669 —670
[31] Wenschuh H , Beyermann M, Haber H , Seydel J K, Krause E ,Bienert M, Carpino L A , El2Faham A , Albericio F. J . Org.Chem. , 1995 , 60 : 405 —410
[32] Bertho J N , Loffet A , Pinel C , Reuther F , Sennyey G.Tetrahedron Lett . , 1991 , 32 : 1303 —1306
[33] Wenschuh H , Beyermann M, Krause E , Brudel M, Winter R ,Schumann M, Carpino L A , Bienert M. J . Org. Chem. , 1994 ,59 : 3275 —3280
[34] Wenschuh H , Beyermann M, Krause E , Carpino L A , Bienert M.Tetrahedron Lett . , 1993 , 34 : 3733 —3736
[35] Carpino L A , El-Faham A. J . Am. Chem. Soc. , 1995 , 117 :5401 —5402
[36] Carpino L A , Ionescu D , El-Faham A , Beyermann M, Henklein P , Hanay C , Wenschuh H , Bienert M. Org. Lett . , 2003 , 5 (7) :975 —977
[37] Carpino L A , Ionescu D , El-Faham A , HenKlein P , Wenschuh H , Bienert M, Beyermann M. Tetrahedron Lett . , 1998 , 39 :241 —244
[38] Miller S C , Scanlan T S. J . Am. Chem. Soc. , 1998 , 120 (11) :2690 —2691
[39] Vedejs E , Kongkittingam C. J . Org. Chem. , 2000 , 65 : 2309 —2318
[40] DalPozzo A , Ni M, Muzi L , Caporale A , et al . J . Org. Chem. ,2002 , 67 (18) : 6372 —6375
[41] Fan C X, Hao X L , Ye Y H. Synth. Commun. , 1996 , 26 :1455 —1460
[42] Xie H B , Tian G L , Ye Y H. Synth. Commun. , 2000 , 30 :4233 —4240
[43] Tang Y C , Xie H B , Tian GL , Ye Y H. J . Pept . Res. , 2002 ,60 : 95 —103
[44] Li H T, Jiang X H , Ye Y H , Fan C X, Romoff T, Goodman M.Org. Lett . , 1999 , 1 : 91 —94
[45] Liu P , Sun B Y, Chen X H , Tian G I , Ye Y H. Synth.Commun. , 2002 , 32 : 473 —480
[46] Goodman M, Zapf C , Rew Y. Biopolymers (Pept . Sci . ) , 2001 ,60 : 229 —245
[47] Boger D L , Kim S H , Mori Y, et al . J . Am. Chem. Soc. ,2001 , 123 : 1862 —1871
[48] JoulliéM M, Portonovo P , Liang B , et al . Tetrahedron Lett . ,2000 , 41 : 9373 —9376
[49] Fu Y, Hammer R P. Org. Lett . , 2002 , 4 (2) : 237 —240
[50] Fu Y, Hammarstrom L G J , Miller T J , Fronczek F R ,McLaughlin M L , Hammer R P. J . Org. Chem. , 2001 , 66 :7118 —7124
[51] Tantry S J , Suresh Babu V V. Lett . Pept . Sci . , 2002 , 9 : 35 —41
[52] Jiang L , Davison A , Tennant G, Ramage R. Tetrahedron , 1998 ,54 : 14233 —14254
[53] Robertson N , Jiang L , Ramage R. Tetrahedron , 1999 , 55 :2713 —2720
[54] Klose J , EI-Faham A , Henkleins P , Carpino L A , Bienert M.Tetrahedron Lett . , 1999 , 40 : 2045 —2048
[55] El-Faham A. Lett . Pept . Sci . , 2000 , 7 : 113 —121
[56] Han S Y, Kim YA. Tetrahedron , 2004 , 60 : 2447 —2467
[1] Wang Zhihui*, Wang Xiao. Synthesis of Azaindoles [J]. Progress in Chemistry, 2012, (10): 1974-1982.
[2] Jiang Yubo, Kuang Chunxiang. Synthesis of 1, 2, 3-Triazole Derivatives [J]. Progress in Chemistry, 2012, (10): 1983-1994.
[3] Hou Chen, Zhu Hao, Li Yijing, Li Yanfeng. Immobilized Proline and Its Derivatives Employed in the Catalysis of Asymmetric Organic Synthesis [J]. Progress in Chemistry, 2012, (9): 1729-1741.
[4] Yue Guizhou, Huang Qianming, Zou Ping. Synthesis of Sesquiterpenoids: Englerin A and Its Analogues [J]. Progress in Chemistry, 2012, (9): 1742-1750.
[5] Shen Jinhai, Cheng Guolin, Cui Xiuling. Domino Reactions Based on Pd-Catalyzed C-H Bond Activation [J]. Progress in Chemistry, 2012, 24(07): 1324-1336.
[6] Bao Chunyan, Jia Huijuan, Liu Tao, Wang Yi, Peng Wei, Zhu Linyong. Synthesis of Artificial Ion Channels in Bilayer Membrane [J]. Progress in Chemistry, 2012, 24(07): 1337-1345.
[7] Weng Jianquan, Yu Zhiqin, Zhang Guofu. Direct Oxidative Coupling Between Unfunctionalized Arene and Olefin [J]. Progress in Chemistry, 2012, 24(04): 523-544.
[8] Liu Yanhong, Zhou Lincheng, Hui Xinping, Zhao Guanghui, Li Yanfeng. Applications of Superparamagnetically Separable Nano-Catalysts in Organic Synthesis [J]. Progress in Chemistry, 2012, 24(0203): 327-337.
[9] Li Gaowei, Wang Xiaojuan, Zhao Wenxian, Lu Liujie, Liu Guanjun, Wang Mincan. Trost-Type Chiral Semi-Azacrown Ether Ligands in Asymmetric Catalysis [J]. Progress in Chemistry, 2012, 24(0203): 348-360.
[10] Zhang Guofu, Wen Xin, Wang Yong, Mo Weimin, Ding Chengrong. Recent Advances in Oxidative Deoximation [J]. Progress in Chemistry, 2012, 24(0203): 361-369.
[11] Cao Jing, Jiang Yi, Chen Chuan-Feng. Advances on Synthesis and Applications of Iptycenes and Their Derivatives [J]. Progress in Chemistry, 2011, 23(11): 2200-2214.
[12] Wang Jue, Zhan Yuexiong, Jiang Biao. Dimeric Pyrrole-Imidazole Alkaloids [J]. Progress in Chemistry, 2011, 23(10): 2065-2078.
[13] Yang Shengyan, Wu Zhenyi, Wan Xinjun, Yan Juan. Synthesis of Porphyrin-Fullerene Complexes [J]. Progress in Chemistry, 2011, 23(6): 1123-1136.
[14] Liu Guannan, Zhou Yu, Jiang Hualiang, Liu Hong. Recent Advances in Silver-Mediated Organic Synthesis Reactions [J]. Progress in Chemistry, 2011, 23(6): 1137-1147.
[15] Yang Liancheng, Qi Xiangyang, Xu Longhe. Formation of P-C Bonds via Palladium-Catalyzed Cross-Coupling Reactions [J]. Progress in Chemistry, 2011, 23(5): 893-902.