Continuous Photochemical Cleavage of Linkers for Solid-Phase Synthesis

被引:23
|
作者
Hurevich, Mattan [1 ]
Kandasamy, Jeyakumar [1 ]
Ponnappa, Bopanna M. [1 ,2 ]
Collot, Mayeul [1 ]
Kopetzki, Daniel [1 ]
McQuade, D. Tyler [1 ,3 ]
Seeberger, Peter H. [1 ,2 ]
机构
[1] Max Planck Inst Colloids & Interfaces, D-14476 Golm, Germany
[2] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
[3] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
关键词
PROTECTING GROUPS; PEPTIDE-SYNTHESIS; PURIFICATION; TRACELESS;
D O I
10.1021/ol500530q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photo labile linkers are an attractive alternative for solid-phase synthesis because they can be cleaved using light. However, irradiation in a classical batch photoreactor results in incomplete cleavage of the photolabile linkers. It is demonstrated that a continuous flow photoreactor is superior to a batch photoreactor for the cleavage of a linker from polystyrene resin.
引用
收藏
页码:1794 / 1797
页数:4
相关论文
共 50 条
  • [21] Triazenes as robust and simple linkers for amines in solid-phase organic synthesis
    Bräse, S
    Köbberling, J
    Enders, D
    Lazny, R
    Wang, MF
    Brandtner, S
    TETRAHEDRON LETTERS, 1999, 40 (11) : 2105 - 2108
  • [22] New fluoride-labile linkers for solid-phase organic synthesis
    Routledge, A
    Stock, HT
    Flitsch, SL
    Turner, NJ
    TETRAHEDRON LETTERS, 1997, 38 (47) : 8287 - 8290
  • [23] Solid-phase synthesis of polyfunctional polylysine dendrons using aldehyde linkers
    Svenssen, Daniel K.
    Mirsharghi, Sahar
    Boas, Ulrik
    TETRAHEDRON LETTERS, 2014, 55 (29) : 3942 - 3945
  • [24] Synthesis and applications of tert-alkoxysiloxane linkers in solid-phase chemistry
    Meloni, Marco M.
    White, Peter D.
    Armour, Duncan
    Brown, Richard C. D.
    TETRAHEDRON, 2007, 63 (02) : 299 - 311
  • [25] Linkers and cleavage strategies for solid phase synthesis. Overview and future prospects
    Carboni, B
    Carreaux, F
    Pilard, JF
    ACTUALITE CHIMIQUE, 2000, (09): : 9 - 13
  • [26] Application of aryloximes as solid-phase ketone linkers
    Lepore, SD
    Wiley, MR
    ORGANIC LETTERS, 2003, 5 (01) : 7 - 10
  • [27] SOLID-PHASE PHOTOCHEMICAL C-S BOND-CLEAVAGE OF THIOETHERS - A NEW APPROACH TO THE SOLID-PHASE PRODUCTION OF NONPEPTIDE MOLECULES
    SUCHOLEIKI, I
    TETRAHEDRON LETTERS, 1994, 35 (40) : 7307 - 7310
  • [28] A new cleavage strategy for the solid-phase synthesis of secondary amines
    Conti, P
    Demont, D
    Cals, J
    Ottenheijm, HCJ
    Leysen, D
    TETRAHEDRON LETTERS, 1997, 38 (16) : 2915 - 2918
  • [29] Fallaxin: Optimization of cleavage conditions following solid-phase synthesis
    Nielsen, S. L.
    Christensen, U.
    Hansen, P. R.
    JOURNAL OF PEPTIDE SCIENCE, 2006, 12 : 129 - 129
  • [30] Novel oxidatively removable protecting groups and linkers for solid-phase synthesis of oligosaccharides
    Fukase, K
    Egusa, K
    Nakai, Y
    Kusumoto, S
    MOLECULAR DIVERSITY, 1997, 2 (04) : 182 - 188