Recent developments in linker design and application

Current Opinion in Chemical Biology

Volumn 7, Issue 3, 2003, Pages 346-352

  Wills, A Jonathan ^a   Balasubramanian, Shankar ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

RESIN;

CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL PARAMETERS; CHEMICAL STRUCTURE; PHYSICAL CHEMISTRY; REGULATORY MECHANISM; REVIEW; SOLID; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038198839     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(03)00035-8     Document Type: Review

References (26)

1. Bradley F., Orain P., Bradley M. Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry. Chem. Rev. 100:2000;2091-2157.
2. Paterson I., Temal-Laïb T. Toward the combinatorial synthesis of polyketide libraries: asymmetric aldol reactions with α-chiral aldehydes on solid support. Org. Lett. 4:2002;2473-2476 Excellent use of a silyl linker in the multi-step synthesis of complex polyketide-type sequences.
3. Meloni M.M., Brown R.C.D., White P.D., Armour D. Novel silyl linkers for solid-phase synthesis. Tetrahedron Lett. 43:2002;6023-6026.
4. Varray S, Lazaro R, Martinez J, Lamatay F: A new soluble polymer-supported sulfonyl linker- application to the synthesis of the cyclic α-amino acids. Eur J Org Chem 2002: 2308-2316.
5. Wagner M., Kunz H. The (2-phenyl-2-trimethylsiyl)ethyl-(PTMSEL) linker- a novel linker for the solid-phase synthesis of protected peptides and glycopeptides cleavable with fluoride. Angew. Chem. Int. Ed. 41:2002;317-321.
6. Guo M., Varaday L. Synthesis of 4-pentenoic and 5-hexenoic acids on polystyrene resin and their use as cleavable linkers. Tetrahedron Lett. 43:2002;5611-5615.
7. Izumi M., Fukase K., Kusumoto S. Solid-phase synthesis of oligosaccharides using novel alkyne-type linkers: selection of reactive sites on the support by Sonigashira reaction. Synlett. 9:2002;1404-1408.
8. McKerlie F, Procter DJ, Wynne G: Reduction of α-aryloxy carbonyl compounds with samarium(II) iodide. A new traceless linker for the solid phase synthesis of carbonyl compounds. Chem Commun 2002:584-585.
9. Raghavan S, Rajender A: Target alcohol/phenol release by cyclative cleavage using glycine as a safety catch linker. Chem Commun 2002:1572-1573.
10. Subra G., Amlard M., Martinez J. Glutamic acid as a new linker for attachment of alcohols to solid support. Tetrahedron Lett. 43:2002;9221-9223.
11. Komatsu M., Okada H., Akaki T., Oderaotoshi Y., Minakata S. Generation and cycloadition of polymer-supported azomethine ylide via a 1,2-silatropic shift of α-silylimines: traceless synthesis of pyrrolidine derivatives. Org. Lett. 4:2002;3505-3508.
12. Porta El., Piarulli U., Cardullo F., Paio A., Provera S., Seneci P., Gennari C. Cyclative cleavage via solid-phase supported stabilized sulfur ylides: synthesis of macrocyclic lactones. Tetrahedron Lett. 43:2002;761-766.
13. Huang X., Liu Z. Solid-phase synthesis of 4(1H)-quinolone and pyrimidine derivatives based on a new scaffold-polymer-bound cyclic malonic ester. J. Org. Chem. 67:2002;6731-6737.
14. Nicolaou K.C., Montagnon T., Ulven T., Baran P.S., Zhong Y.-L., Sarabia F. Novel chemistry of α-tosyl ketones: application to the solution- and solid-phase synthesis of privileged heterocycle and enediyne libraries. J. Am. Chem. Soc. 124:2002;5718-5728 The use of a new linker system to access a large range of heterocyclic scaffolds in a minimal number of steps. Notable for the simplicity of the linker system and the range of chemistries employed in the exemplification.
15. Kohli R.M., Walsh C.T., Burkart M.D. Biomimetic synthesis and optimisation of cyclic peptide antibiotics. Nature. 418:2002;658-661 The use of an excised thioesterase enzyme to catalyse the cleavage and cyclisation of a polymer-bound decapeptide. The use of the enzyme is extended to other decapeptides in the synthesis of a library of compounds for antibiotic activity.
16. Savinov S.N., Austin D.J. Diastereofacial solid phase synthesis and promoted cleavage of a [2.2.1] bicyclic scaffold. Org. Lett. 4:2002;1419-1422.
17. Wills A.J., Krishnan-Ghosh Y., Balasubramanian S. Synthesis of a polymer-supported oxazolidine aldehyde for asymmetric chemistry. J. Org. Chem. 67:2002;6646-6652.
18. Nakamura S., Uchiyama Y., Ishikawa S., Fukinbara R., Watanabe Y., Toru T. Asymmetric conjugate addition reactions of polymer-supported highly enantioenriched β-(trimethylsilyl)ethyl sulfoxides. Tetrahedron Lett. 43:2002;2381-2383.
19. 13C NMR J. Am. Chem. Soc. 124:2002;3591-3599.
20. Cano M., Ladlow M., Balasubramanian S. Studies on the stability and functional group compatibility of the benzoin photolabile safety-catch linker using an analytical construct. J. Comb. Chem. 4:2002;44-48 The use of an analytical linker system in the rapid identification of reaction conditions likely to cleave the benzoin linker construct. Generally useful method for characterizing new linkers.
21. Elsayed G.A., Zhu T., Boons G.-J. Demixing libraries of saccharides using a multi-linker approach in combination with a soluble polymeric support. Tetrahedron Lett. 43:2002;4691-4694 A method for deconvoluting libraries based upon simple chemical orthogonality between purposely designed linkers. This approach was successfully demonstrated in the separation of an oligosaccharide array.
22. Pon R.T., Yu S., Sanghvi Y.S. Tandem oligonucleotide synthesis on solid-phase supports for the production of multiple oligonucleotides. J. Org. Chem. 67:2002;856-864.
23. Okada H., Akaki T., Oderaotoshi Y., Minakata S., Komatsu M. Generation and cycloaddition of polymer-supported azomethine ylide by utilizing the characteristics of silicon: a facile route to pyrrolidines and pyrroles from α-silylimines bound to resin. Tetrahedron. 59:2003;197-205.
24. Hutchison P.C., Heightman T.D., Procter D.J. Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase. Org. Lett. 4:2002;4583-4585.
25. Galtz H., Bannwarth W. A new versatile linker for the solid-phase synthesis of secondary amines. Tetrahedron Lett. 44:2003;149-152.
26. Lepore S.D., Wiley M.R. Application of aryloximes as solid-phase ketone linkers. Org. Lett. 5:2003;7-10.