Ring-Closing Metathesis Approaches for the Solid-Phase Synthesis of Cyclic Peptoids

被引:46
|
作者
Khan, Sharaf Nawaz [1 ]
Kim, Arim [1 ]
Grubbs, Robert H. [2 ]
Kwon, Yong-Uk [1 ]
机构
[1] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 120750, South Korea
[2] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Lab Chem Synth, Pasadena, CA 91125 USA
关键词
PASSIVE MEMBRANE-PERMEABILITY; OLEFIN METATHESIS; PEPTIDOMIMETIC OLIGOMERS; BIOACTIVE PEPTIDES; DICARBA-ANALOGS; SURROGATE; CONSTRUCTION; INHIBITOR; HELICES; ACID;
D O I
10.1021/ol200226z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclic peptoids were efficiently synthesized on a solid phase in high yields utilizing ring-closing metathesis (RCM). This method should be a valuable tool for easy access to cyclic peptoid libraries and various cyclic compounds.
引用
收藏
页码:1582 / 1585
页数:4
相关论文
共 50 条
  • [21] Synthesis of Sultams by Ring-Closing Metathesis
    Mondal, Shovan
    Debnath, Sudarshan
    [J]. SYNTHESIS-STUTTGART, 2014, 46 (03): : 368 - 374
  • [22] Parallel Solid-Phase Synthesis of Macrocyclic Peptidomimetics Using Ru-Catalyzed Ring-Closing Metathesis and a New Application of Cross Metathesis
    Beaubien, Sylvie
    Hoveyda, Hamid R.
    Vezina, Martin
    Marsault, Eric
    Tremblay, Hugo
    Foucher, Laurence
    Benakli, Kamel
    [J]. PEPTIDES FOR YOUTH, 2009, 611 : 13 - 14
  • [23] Synthesis of cyclic sulfamoyl carbamates and ureas via ring-closing metathesis
    Dougherty, JM
    Jiménez, M
    Hanson, PR
    [J]. TETRAHEDRON, 2005, 61 (26) : 6218 - 6230
  • [24] Synthesis of constrained cyclic peptide helices by ring-closing metathesis.
    Blackwell, HE
    Grubbs, RH
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U22 - U23
  • [25] Ring-closing alkyne metathesis mediated synthesis of cyclic β-turn mimetics
    IJsselstijn, M
    Aguilera, B
    van der Marel, GA
    van Boom, JH
    van Delft, FL
    Schoemaker, HE
    Overkleeft, HS
    Rutjes, FPJT
    Overhand, M
    [J]. TETRAHEDRON LETTERS, 2004, 45 (22) : 4379 - 4382
  • [26] Ring-closing metathesis strategies to cyclic sulfamide peptidomimetics
    Dougherty, JM
    Probst, DA
    Robinson, RE
    Moore, JD
    Klein, TA
    Snelgrove, KA
    Hanson, PR
    [J]. TETRAHEDRON, 2000, 56 (50) : 9781 - 9790
  • [27] Cyclic sulfonamides via the ring-closing metathesis reaction
    Hanson, PR
    Probst, DA
    Robinson, RE
    Yau, M
    [J]. TETRAHEDRON LETTERS, 1999, 40 (26) : 4761 - 4764
  • [28] Ring-closing metathesis strategies to cyclic sulfamides.
    Dougherty, JM
    Probst, DA
    Hanson, PR
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U107 - U107
  • [29] Reversible backbone protection enables combinatorial solid-phase ring-closing metathesis reaction (RCM) in peptides
    Schmiedeberg, N
    Kessler, H
    [J]. ORGANIC LETTERS, 2002, 4 (01) : 59 - 62
  • [30] A ring-closing metathesis approach to cyclic α,β-dehydroamino acids
    Hekking, Koen F. W.
    Waalboer, Dennis C. J.
    Moelands, Marcel A. H.
    van Delft, Floris L.
    Rutjes, Floris P. J. T.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (01) : 95 - 106