Facile and purification free synthesis of peptides utilizing ROMPgel- and ROMPsphere-supported coupling reagents

被引:15
作者
Barrett, AGM [1 ]
Bibal, B [1 ]
Hopkins, BT [1 ]
Köbberling, J [1 ]
Love, AC [1 ]
Tedeschi, L [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
基金
英国工程与自然科学研究理事会;
关键词
acylations; combinatorial chemistry; peptides; parallel synthesis; supported reagents;
D O I
10.1016/j.tet.2005.06.120
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Norbomene-2-carboxaldehyde and norbornadiene were respectively converted into norbornene derivatives functionalized with fluoroformamidinium hexafluorophosphate and 2-bromo-N-methylpyridinium tetrafluoroborate residues. Both these norbomene monomers were ring opening metathesis polymerized or graft copolymerized onto polystyrene cores to produce ROMPgel and ROMPsphere peptide-coupling reagents. These were used to prepare hindered amides, dipeptides and tripeptides with minimal purification in parallel arrays. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:12033 / 12041
页数:9
相关论文
共 107 条
  • [1] Abraham S, 1998, POLYM INT, V45, P271, DOI 10.1002/(SICI)1097-0126(199803)45:3<271::AID-PI916>3.0.CO
  • [2] 2-E
  • [3] PALLADIUM-CATALYZED PREPARATION OF EXO-ARYL DERIVATIVES OF THE NORBORNANE SKELETON
    ARCADI, A
    MARINELLI, F
    BERNOCCHI, E
    CACCHI, S
    ORTAR, G
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 368 (02) : 249 - 256
  • [4] ROMPgel-supported biphenyl and naphthalene: reagents for lithiation reactions with minimal purification
    Arnauld, T
    Barrett, AGM
    Hopkins, BT
    [J]. TETRAHEDRON LETTERS, 2002, 43 (06) : 1081 - 1083
  • [5] Facile and purification free synthesis of Mosher amides utilizing a ROMPgel supported reagent
    Arnauld, T
    Barrett, AGM
    Hopkins, BT
    Zécri, FJ
    [J]. TETRAHEDRON LETTERS, 2001, 42 (46) : 8215 - 8217
  • [6] ROMPGEL scavengers:: A high-loading supported anhydride for sequestering amines and hydrazines
    Arnauld, T
    Barrett, AGM
    Cramp, SM
    Roberts, RS
    Zécri, FJ
    [J]. ORGANIC LETTERS, 2000, 2 (17) : 2663 - 2666
  • [7] ROMPgel supported allylboronate: a purification-free method for the preparation of homoallylic alcohols
    Arnauld, T
    Barrett, AGM
    Seifried, R
    [J]. TETRAHEDRON LETTERS, 2001, 42 (44) : 7899 - 7901
  • [8] ROMPgel-supported tris(triphenylphosphine)rhodium(I) chloride:: a selective hydrogenation catalyst for parallel synthesis
    Årstad, E
    Barrett, AGM
    Tedeschi, L
    [J]. TETRAHEDRON LETTERS, 2003, 44 (13) : 2703 - 2707
  • [9] ROMPgel-supported triphenylphosphine with potential application in parallel synthesis
    Årstad, E
    Barrett, AGM
    Hopkins, BT
    Köbberling, J
    [J]. ORGANIC LETTERS, 2002, 4 (11) : 1975 - 1977
  • [10] 2-mercaptopyridone 1-oxide-based uronium salts:: New peptide coupling reagents
    Bailén, MA
    Chinchilla, R
    Dodsworth, DJ
    Nájera, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) : 8936 - 8939