Solid phase synthesis - Designer linkers for combinatorial chemistry: A review

Journal of Chemical Technology and Biotechnology

Volumn 74, Issue 9, 1999, Pages 835-851

  Gordon, Kirsteen ^a   Balasubramanian, Shankar ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Combinatorial chemistry; Linker; Solid phase synthesis

Indexed keywords

BENZENE; BIOCOMPATIBILITY; CHEMICAL BONDS; ENZYMES; NITROGEN COMPOUNDS; ORGANIC SOLVENTS; PHOTOLYSIS; RESINS;

COMBINATORIAL CHEMISTRY; LINKERS; SOLID PHASE SYNTHESIS;

SYNTHESIS (CHEMICAL);

ALCOHOL; ALKENE; AMINE; AROMATIC COMPOUND; BENZODIAZEPINE; CARBON; CARBONYL DERIVATIVE; CYCLOPEPTIDE; ENZYME; ORGANIC COMPOUND; OXAZOLIDINE DERIVATIVE; PALLADIUM COMPLEX; POLYMER; RESIN; SILANE DERIVATIVE; SILICON; SULFUR; TERTIARY AMINE; TETRAPEPTIDE;

BIOCOMPATIBILITY; CHEMICAL BINDING; CHIRALITY; CROSS LINKING; METHODOLOGY; ORGANIC CHEMISTRY; PEPTIDE SYNTHESIS; PHYSICAL PHASE; PROTEIN DEGRADATION; REVIEW; SOLID; SYNTHESIS;

EID: 0032884952     PISSN: 02682575     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-4660(199909)74:9<835::aid-jctb130>3.0.co;2-z     Document Type: Review

References (91)

1. Merrifield RB, Solid phase synthesis I. The synthesis of a Tetrapeptide. J Am Chem Soc 85:2149-2154 (1963).
2. Wunsch E, Synthesis of naturally occurring polypeptides, problems of current research. Angew Chem Int Ed 10:786-795 (1971).
3. Caruthers MH, Gene synthesis machinery: DNA chemistry and its uses. Science 230:281-285 (1985).
4. Danishefsky SJ, McClure KF, Randolph JT and Ruggeri RB, A strategy for the solid-phase synthesis of oligosaccharides. Science 260:1307-1309 (1993).
5. Schuster M, Wang P, Paulson JC and Wong CH, Solid-phase chemical-enzymatic synthesis of glycopeptides and oligosaccharides. J Am Chem Soc 116:1135-1136 (1994).
6. Balkenhohl F, Vondembusschehunnefeld C, Lansky A and Zechel C, Combinatorial synthesis of small organic-molecules. Angew Chem Int Ed 35:2289-2337 (1996).
7. Brown RCD, Recent developments in solid-phase organic synthesis. Journal of the Chemical Society-Perkin Transactions 1 3293-3320 (1998).
8. Brown AR, Hermkens PHH, Ottenheijm HCJ and Rees DC, Solid phase synthesis. Synlett (8) 817 (1998).
9. Fruchtel JS and Jung G, Organic-chemistry on solid supports. Angew Chem Int Ed 35:17-42 (1996).
10. Thompson LA and Ellman JA, Synthesis and applications of small molecule libraries. Chem Rev 96:555-600 (1996).
11. Terrett NK, Gardner M, Gordon DW, Kobylecki RJ and Steele J, Combinatorial synthesis - the design of compound libraries and their application to drug discovery. Tetrahedron 51:8135-8173 (1995).
12. Geysen HM, Meleon SJ and Barteling SJ, Use of peptide synthesis to probe viral antigens for epitopes to a resolution of a single amino acid. Proc Natl Acad Sci USA 81:3998-4002 (1984).
13. Houghten RA, General method for the rapid solid-phase synthesis of large numbers of peptides: specificity of antigen-antibody interaction at the level of individual amino acids. Proc Natl Acad Sci USA 82:5131-5135 (1985).
14. Sebestyen F, Dibo G, Kovacs A and Furka A, Chemical synthesis of peptide libraries. Bioorg Med Chem Lett 3:413-418 (1993).
15. Furka A, Sebestyen F, Asgedom M and Dibo G, General-method for synthesis of multicomponent peptide mixtures. Int J Pep Prot Res 37:487-493 (1991).
16. Lam KS, Salmon SE, Hersh EM, Hruby VJ, Kazmierski WM and Knapp RJ, A new type of synthetic peptide library for identifying ligand-binding activity. Nature 354:82-84 (1991).
17. Simon RJ, Kania RS, Zuckermann RN, Huebner VD, Jewell DA, Banville S, Ng S, Wang L, Rosenberg S, Marlowe CK, Spellmeyer DC, Tan RY, Frankel AD, Santi DV, Cohen FE and Bartlett PA, Peptoids a modular approach to drug discovery. Proc Natl Acad Sci USA 89:9367-9371 (1992).
18. Cho CY, Moran EJ, Cherry SR, Stephans JC, Fodor SPA, Adams CL, Sundaram A, Jacobs JW and Schultz PG, An unnatural biopolymer. Science 261:1303-1305 (1993).
19. Gennari C, Salom B, Potenza D and Williams A, Synthesis of sulfonamido-pseudopeptides new chiral unnatural oligomers. Angew Chem Int Ed 33:2067-2069 (1994).
20. Gennari C, Nestler HP, Salom B and Still WC, Synthetic receptors based on vinylogous sulfonyl peptides. Angew Chem Int Ed 34:1765-1768 (1995).
21. Bunin BA and Ellman JA, A general and expedient method for the solid-phase synthesis of 1,4-benzodiazepine derivatives. J Am Chem Soc 114:10997-10998 (1992).
22. Leznoff CC, The use of insoluble polymer supports in organic synthesis. Acc Chem Res 11:327-333 (1978).
23. Wong JY, Manning C and Leznoff CC, Solid phase synthesis and photochemistry of 4.4'-stilbenedicarbaldehyde. Angew Chem Int Ed 13:666-667 (1974).
24. Crowley JI and Rapoport H, Solid-phase organic synthesis: novelty of fundamental concept. Acc Chem Res 9:135-144 (1976).
25. Fridkin M, Patchornik A and Katchalski E, A synthesis of cyclic peptides utilising high molecular weight carriers. J Am Chem Soc 87:4646-4648 (1965).
26. Frechet JMJ, Synthesis and applications of organic polymers as supports and protecting groups. Tetrahedron 37:663-683 (1981).
27. Hermkens PHH, Ottenheijm HCJ and Rees D, Solid-phase organic-reactions - a review of the recent literature. Tetrahedron 52:4527-4554 (1996).
28. Hermkens PHH, Ottenheijm HCJ and Rees DC, Solid-phase organic reactions .2. A review of the literature Nov 95-Nov 96. Tetrahedron 53:5643-5678 (1997).
29. Lacombe P, Castagner B, Gareau Y and Ruel R, Reduction of olefins on solid support using diimide. Tetrahedron Lett 39:6785-6786 (1998).
30. Shapiro MJ and Wareing JR, NMR methods in combinatorial chemistry. Current Opinion In Chemical Biology 2:372-375 (1998).
31. Wells NJ, Davies M and Bradley M, Cleavage and analysis of material from single resin beads. J Org Chem 63:6430-6431 (1998).
32. Swali V, Wells NJ, Langley GJ and Bradley M, Solid-phase dendrimer synthesis and the generation of super-high-loading resin beads for combinatorial chemistry. J Org Chem 62:4902-4903 (1997).
33. Wang S, p-Alkoxybenzyl alcohol resin and p-alkoxybenzyloxy-carbonylhydrazide resin for solid phase synthesis of protected peptide fragments. J Am Chem Soc 95:1328-1333 (1973).
34. Baltrop JA, Plant PJ and Schofield P, Photosensitive protecting groups. Chemical Communications 22:822-823 (1966).
35. Rich DH and Gurwara SK, Removal of protected peptides from an o-nitrobenzyl resin by photolysis. Chemical Communications (17) 610-611 (1973).
36. Rich DH and Gurwara SK, Preparation of a new o-nitrobenzyl resin for solid phase synthesis of t-butyloxycarbonyl protected peptide acids. J Am Chem Soc 97:1575-1579 (1975).
37. Ajayaghosh A and Pillai VNR, Polymer-supported synthesis of protected peptide segments on a photosensitive omicron-nitro(alpha-methyl)bromobenzyl resin. Tetrahedron 44:6661-6666 (1988).
38. Holmes CP and Jones DG, Reagents for combinatorial organic-synthesis - development of a new O-Nitrobenzyl photolabile linker for solid-phase synthesis. J Org Chem 60:2318-2319 (1995).
39. Whitehouse DL, Savinov SN and Austin DJ, An improved synthesis and selective coupling of a hydroxy based photolabile linker for solid phase organic synthesis. Tetrahedron Lett 38:7851-7852 (1997).
40. Yoo DJ and Greenberg MM, Synthesis of oligonucleotides containing 3′-alkyl carboxylic-acids using universal, photolabile solid-phase synthesis supports. J Org Chem 60:3358-3364 (1995).
41. Routledge A, Abell C and Balasubramanian S, The use of a dithiane protected benzoin photolabile safety catch linker for solid-phase synthesis. Tetrahedron Lett 38:1227-1230 (1997).
42. Kenner GW, McDermott JR and Sheppard RC, The safety catch principle in solid phase peptide synthesis. Chemical Communications (12) 636-637 (1971).
43. Backes BJ and Ellman JA, Carbon-Carbon bond-forming methods on solid support - utilization of Kenner safety-catch linker. J Am Chem Soc 116:11171-11172 (1994).
44. Backes BJ, Virgilio AA and Ellman JA, Activation method to prepare a highly reactive acylsulfonamide safety-catch linker for solid-phase synthesis. J Am Chem Soc 118:3055-3056 (1996).
45. Hauske JR and Dorff P, A solid-phase Cbz chloride equivalent -a new matrix specific linker. Tetrahedron Lett 36:1589-1592 (1995).
46. Marsh IR, Smith HK, LeBlanc C and Bradley M, Synthetic methods for polyamine linkers and their application to combinatorial chemistry. Molecular Diversity 2:165-170 (1997).
47. Thompson LA and Ellman JA, Straightforward and general-method for coupling alcohols to solid supports. Tetrahedron Lett 35:9333-9336 (1994).
48. Yoo S, Seo J, Yi K and Gong Y, Solid phase synthesis of biphenyltetrazole derivatives. Tetrahedron Lett 38:1203-1206 (1997).
49. Liu GC and Ellman JA, A general solid-phase synthesis strategy for the preparation of 2-pyrrolidinemethanol ligands. J Org Chem 60:7712-7713 (1995).
50. Koh JS and Ellman JA, Palladium-mediated three-component coupling strategy for the solid-phase synthesis of tropane derivatives. J Org Chem 61:4494-4495 (1996).
51. Nugiel DA, Cornelius LAM and Corbett JW, Facile preparation of 2,6-disubstituted purines using solid-phase chemistry. J Org Chem 62:201-203 (1997).
52. Dewitt SH, Kiely JS, Stankovic CJ, Schroeder MC, Cody DMR and Pavia MR, Diversomers-an approach to nonpeptide, nonoligomeric chemical diversity. Proc Natl Acad Sci USA 90:6909-6913 (1993).
53. Dressman BA, Spangle LA and Kaldor SW, Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization cleavage step. Tetrahedron Lett 37:937-940 (1996).
54. Buchstaller HP, Solid phase synthesis of oxazolidinones via a novel cyclisation/cleavage reaction. Tetrahedron 54:3465-3470 (1998).
55. Moon H, Schore NE and Kurth MJ, A polymer-supported C-2-symmetrical chiral auxiliary - preparation of non-racemic 3,5-disubstituted-gamma-butyrolactones. Tetrahedron Lett 35:8915-8918 (1994).
56. Mayer JP, Zhang JW, Bjergarde K, Lenz DM and Gaudino JJ, Solid phase synthesis of 1,4-benzodiazepine-2,5-diones. Tetrahedron Lett 37:8081-8084 (1996).
57. Smith AL, Thomson CG and Leeson PD, An efficient solid phase synthetic route to 1,3-disubstituted 2,4(1H,3H)-quinazolinediones suitable for combinatorial synthesis. Bioorg Med Chem Lett 6:1483-1486 (1996).
58. Beebe X, Schore NE and Kurth MJ, Polymer-supported synthesis Of 2,5-disubstituted tetrahydrofurans. J Am Chem Soc 114:10061-10062 (1992).
59. Miller SJ, Blackwell HE and Grubbs RH, Application of ring-closing metathesis to the synthesis of rigidified amino acids and peptides. J Am Chem Soc 118:9606-9614 (1996).
60. van Maarseveen JH, denHartog JAJ, Engelen V, Finner E, Visser G and Kruse CG, Solid phase ring-closing metathesis: cyclization/cleavage approach towards a seven membered cycloolefin. Tetrahedron Lett 37:8249-8252 (1996).
61. Piscopio AD, Miller JF and Koch K, Solid phase heterocyclic synthesis via ring closing metathesis: traceless linking and cyclative cleavage through a carbon-carbon double bond. Tetrahedron Lett 38:7143-7146 (1997).
62. Piscopio AD, Miller JF and Koch K, A second generation solid phase approach to Freidinger lactams: application of Fukuyama's amine synthesis and cyclative release via ring closing metathesis. Tetrahedron Lett 39:2667-2670 (1998).
63. Plunkett MJ and Ellman JA, A silicon-based linker for traceless solid-phase synthesis. J Org Chem 60:6006-6007 (1995).
64. Chenera B, Finkelstein JA and Veber DF, Protodetachable arylsilane polymer linkages for use in solid-phase organic-synthesis. J Am Chem Soc 117:11999-12000 (1995).
65. Boehm TL and Showalter HDH, Development of a novel silyl ether linker for solid-phase organic-synthesis. J Org Chem 61:6498-6499 (1996).
66. Woolard FX, Paetsch J and Ellman JA, A silicon linker for direct loading of aromatic compounds to supports. Traceless synthesis of pyridine-based tricyclics. J Org Chem 62:6102-6103 (1997).
67. Gowravaram MR and Gallop MA, 'Traceless' solid-phase synthesis of furans via 1,3-dipolar cycloaddition reactions of isomunchnones. Tetrahedron Lett 38:6973-6976 (1997).
68. Ley SV, Mynett DM and Koot WJ, Solid-phase synthesis of bicyclo[2.2.2]octane derivatives via tandem Michael addition-reactions and subsequent reductive amination. Synlett (10) 17-20 (1995).
69. Gayo LM and Suto MJ, Traceless linker: oxidative activation and displacement of a sulfur-based linker. Tetrahedron Lett 38:211-214 (1997).
70. Schurer SC and Blechert S, Ruthenium-catalyzed yne-ene cross metathesis binding to solid support and cleavage by Pd-O-catalysis. Synlett (2) 166 (1998).
71. Morphy JR, Rankovic Z and Rees DC, A novel linker strategy for solid-phase synthesis. Tetrahedron Lett 37:3209-3212 (1996).
72. Brown AR, Rees DC, Rankovic Z and Morphy JR, Synthesis of tertiary amines using a polystyrene (REM) resin. J Am Chem Soc 119:3288-3295 (1997).
73. Ouyang XH, Armstrong RW and Murphy MM, A novel cleavage technique to generate small molecule compounds and libraries via a two-resin system. J Org Chem 63:1027-1032 (1998).
74. Kroll FEK, Morphy R, Rees D and Gani D, Resin-immobilised benzyl and aryl vinyl sulfones: new versatile traceless linkers for solid-phase organic synthesis. Tetrahedron Lett 38:8573-8576 (1997).
75. Kawana M and Emoto S, Asymmetric synthesis on an insoluble polymer support. Tetrahedron Lett 48:4855-4858 (1972).
76. Worster PM, McArthur CR and Leznoff CC, Asymmetric synthesis of 2-alkylcyclohexanones on solid phases. Angew Chem Int Ed 18:221-222 (1979).
77. Moon HS, Schore NE and Kurth MJ, A polymer-supported chiral auxiliary applied to the iodolactonization reaction-preparation of gamma-butyrolactones. J Org Chem 57:6088-6089 (1992).
78. Allin SM and Shuttleworth SJ, The preparation and first application of a polymer-supported Evans oxazolidinone. Tetrahedron Lett 37:8023-8026 (1996).
79. Burgess K and Lim D, Resin type can have important effects on solid phase asymmetric alkylation reactions. Chemical Communications (8) 785-786 (1997).
80. Purandare AV and Natarajan S, Synthesis of chiral alpha-substituted beta-hydroxy acid derivatives on solid support. Tetrahedron Lett 38:8777-8780 (1997).
81. Phoon CW and Abell C, Solid phase aldol and conjugate addition reactions using Evans' oxazolidinone chiral auxiliary. Tetrahedron Lett 39:2655-2658 (1998).
82. Winkler JD and McCoull W, Diels-Alder reaction on solid supports using polymer-bound oxazolidinones. Tetrahedron Lett 39:4935-4936 (1998).
83. Reggelin M and Brenig V, Towards polyketide libraries - iterative, asymmetric aldol reactions on a solid support. Tetrahedron Lett 37:6851-6852 (1996).
84. Reggelin M, Brenig V and Welcker R, Towards polyketide libraries - II: Synthesis of chiral aracemic di- and triketides on a solid support. Tetrahedron Lett 39:4801-4804 (1998).
85. Kocis P, Krchnak V and Lebl M, Symmetrical structure allowing the selective multiple release of a defined quantity of peptide from a single bead of polymeric support. Tetrahedron Lett 34:7251-7252 (1993).
86. Cardno M and Bradley M, A simple multiple release system for combinatorial library and peptide analysis. Tetrahedron Lett 37:135-138 (1996).
87. Baldwin JJ, Burbaum JJ, Henderson I and Ohlmeyer MHJ, Synthesis of a small-molecule combinatorial library encoded with molecular tags. J Am Chem Soc 117:5588-5589 (1995).
88. Hoffmann S and Frank R, A new safety-catch peptide-resin linkage for the direct release of peptides into aqueous buffers. Tetrahedron Lett 35:7763-7766 (1994).
89. Panke G and Frank R, Improved preparation of a safety-catch linker for the solid phase synthesis of peptide acids finally released into aqueous buffers. Tetrahedron Lett 39:17-18 (1998).
90. Atrash B and Bradley M, A pH cleavable linker for zone diffusion assays and single bead solution screens in combinatorial chemistry. Chemical Communications (15) 1397-1398 (1997).
91. Sauerbrei B, Jungmann V and Waldmann H, An enzyme-labile linker group for organic syntheses on solid supports. Angew Chem Int Ed 37:1143-1146 (1998).