Solid support linker strategies

Current Opinion in Chemical Biology

Volumn 1, Issue 1, 1997, Pages 86-93

  Backes, Bradley J ^a   Ellman, Jonathan A ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ORGANIC CHEMISTRY; PHOTOCHEMISTRY; REVIEW;

CHEMISTRY, ORGANIC; INDICATORS AND REAGENTS; PHOTOCHEMISTRY;

EID: 0031151975     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/s1367-5931(97)80113-5     Document Type: Article

References (92)

1. Gallop MA, Barrett RW, Dower WJ, Fodor SPA, Gordon EM: Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries. J Med Chem 1994, 37:1233-1251.
2. Gordon EM, Barrett RW, Dower WJ, Fodor SPA, Gallop MA: Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions. J Med Chem 1994, 37:1385-1401.
3. Czarnik AW, Ellman JA (Eds,): Special issue: combinatorial chemistry. Accounts Chem Res 1996, 29:112-170. This issue includes articles describing several applications of library strategies, including materials science, molecular recognition, and therapeutics.
4. Thompson LA, Ellman JA: Synthesis and applications of small molecule libraries. Chem Rev 1996, 96:555-600. Library synthesis and evaluation strategies, as well as solution- and solid-phase methods to prepare small compound libraries, are reviewed.
5. Balkenhohl F, von dem Bussche-Hünnefeld C, Lansky A, Zechel C: Combinatorial synthesis of small molecule libraries. Angew Chem Int Ed 1996, 35:2288-2337. Library synthesis and evaluation strategies, as well as solution- and solid-phase methods to prepare small compound libraries, are reviewed.
6. Merrifield RB: Solid phase peptide synthesis I. The synthesis of a tetrapeptide. J Am Chem Soc 1963, 85:2149-2150.
7. Lloyd-Williams P, Albericio F, Giralt E: Convergent solid-phase peptide synthesis. Tetrahedron 1993, 49:11065-11133.
8. Barany G, Merrifield RB: Solid phase peptide synthesis. In The Peptides. Edited by Gross E, Meienhofer J. New York: Academic Press, Inc; 1980:43-55.
9. 1H NMR spectra of support-bound componds using different combinations of resins, linkers and solvents were evaluated. The findings suggest that polymer and linker combinations that provide a longer tether, and therefore increased substrate mobility, provide superior spectra.
10. Leznoff CC, Wong JY: The use of polymer supports in organic synthesis. The synthesis of monotrityl ethers of symmetrical diols. Can J Chem 1972, 50:2892-2893.
11. Fréchet JM, Nuyens LJ: The use of polymers as protecting groups in organic synthesis. III. Selective functionalization of polyhydroxyl alcohols. Can J Chem 1976, 54:926-934.
12. Fyles TM, Leznoff CC: The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols. Can J Chem 1976, 54:935-942.
13. Thompson LA, Ellman JA: Straightforward and general method for coupling alcohols to solid-supports. Tetrahedron Lett 1994, 35:9333-9336.
14. 2 symmetric inhibitors of HIV protease containing diamino diol and diamino alcohol cores. J Med Chem 1995, 38:2995-3002.
15. Wong JY, Manning C, Leznoff CC: Solid phase synthesis and photochemistry of 4,4′-stilbenedicarbaldehyde. Angew Chem Int Ed 1974, 13:666-667.
16. Randolph JT, McClure KF, Danishefsky SJ: Major simplifications in oligosaccharide syntheses arising from a solid-phase based method: an application to the synthesis of the Lewis b antigen. J Am Chem Soc 1995, 117:5712-5719.
17. Chan TH, Huang WQ: Polymer-anchored organosilyl protecting group in organic synthesis. J Chem Soc Chem Commun 1985:909-911.
18. Alsina J, Chiva C, Ortiz M, Rabanal F, Giralt E, Albericio F: Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides. Tetrahedron Lett 1997, 38:883-886.
19. Sarshar S, Siev D, Mjalli AMM: Imidazole libraries on solid support. Tetrahedron Lett 1996, 37:835-838.
20. Letsinger RL, Kornet MJ: Popcorn polymer as a support in multistep syntheses. J Am Chem Soc 1963, 85:3045-3046.
21. Felix AM, Merrifield RB: Azide solid phase peptide synthesis. J Am Chem Soc 1970, 92:1385-1391.
22. Hauske JR, Dorff P: A solid phase CBZ chloride equivalent - a new matrix specific linker. Tetrahedron Lett 1995, 36:1589-1592.
23. Kaljuste K, Undén A: Solid phase synthesis of 1,2,3,4-tetrahydro-β-carbolines; implications for combinatorial chemistry. Tetrahedron Lett 1995, 36:9211-9214.
24. Alsina J, Rabanal F, Giralt E, Albericio F: Solid-phase synthesis of "head-to-tail" cyclic peptides via lysine side-chain anchoring. Tetrahedron Lett 1994, 35:9633-9636.
25. Kaljuste K, Undén A: Solid-phase synthesis of peptide aminoalkylamides using an allyl linker. Tetrahedron Lett 1996, 37:3031-3034.
26. Bannwarth W, Huebscher J, Barner R: A new linker for primary amines applicable to combinatorial approaches. Bioorg Med Chem Lett 1996, 6:1525-1528.
27. Nugiel DA, Cornelius LAM, Corbett JW: Facile preparation of 2,6-disubstituted purines using solid-phase chemistry. J Org Chem 1997, 62:201-203.
28. Boojamara CG, Burow KM, Ellman JA: An expedient and high-yielding method for the solid-phase synthesis of diverse 1,4-benzodiazepine-2,5-diones. J Org Chem 1995, 60:5742-5743.
29. t chemistry. J Chem Soc Chem Commun 1995:1475-1476.
30. Krchňák V, Weichsel AS, Cabel D, Flegelova Z, Lebl M: Structurally homogeneous and heterogeneous synthetic combinatorial libraries. Mol Divers 1995, 1:149-164.
31. Kick EK, Ellman JA: Expedient method for the solid-phase synthesis of aspartic acid protease inhibitors directed toward the generation of libraries. J Med Chem 1995, 38:1427-1430.
32. Floyd CD, Lewis CN, Patel SR, Whittaker M: A method for the synthesis of hydroxamic acids on solid phase. Tetrahedron Lett 1996. 37:8045-8048.
33. Richter LS, Desai MC: A TFA-cleavable linkage for solid-phase synthesis of hydroxamic acids. Tetrahedron Lett 1997, 38:321-322.
34. Beaver KA, Siegmund AC, Spear KL: Application of the sulfonamide functional group as an anchor for solid phase organic synthesis (SPOS). Tetrahedron Lett 1996, 37:1145-1148.
35. Ngu K, Patel DV: Preparation of acid-labile resins with halide linkers and their utility in solid phase organic synthesis. Tetrahedron Lett 1997, 38:973-976.
36. Murphy AM, Dagnino R Jr, Vallar PL, Trippe AJ, Sherman SL, Lumpkin RH, Tamura SY, Webb TR: Automated synthesis of peptide C-terminal aldehydes. J Am Chem Soc 1992, 114:3156-3157.
37. Zhang C, Mjalli AMM: A combinatorial method for the solid phase synthesis of α-amino phosphonates and phosphonic acids. Tetrahedron Lett 1996, 37:5457-5460.
38. Cao X, Mjalli AMM: Combinatorial method for the synthesis of α-hydroxy phosphonates on Wang resin. Tetrahedron Lett 1996, 37:6073-6076.
39. Plunkett MJ, Ellman JA: A silicon-based linker for traceless solid-phase synthesis. J Org Chem 1995, 60:6006-6007. An early demonstration of traceless synthesis employing an arylsilane-based linkage for benzodiazepine synthesis is described.
40. Plunkett MJ, Ellman JA: Germanium and silicon linking strategies for traceless solid-phase synthesis. J Org Chem 1997. in press.
41. Chenera B, Finkelstein JA, Veber DF: Protodetachable arylsilane polymer linkages for use in solid phase organic synthesis. J Am Chem Soc 1995, 117:11999-12000.
42. 2, ICI and TFA, to prepare bromine, iodine and hydrogen substituted aryl products is demonstrated.
43. Boehm TL, Showalter HDH: Development of a novel silyl ether linker for solid-phase organic synthesis. J Org Chem 1996, 61:6498-6499.
44. Sucholeiki I: Solid-phase photochemical C-S bond cleavage of thioethers - a new approach to the solid-phase production of non-peptide molecules. Tetrahedron Lett 1994, 35:7307-7310.
45. Zhao XY, Jung KW, Janda KD: Soluble polymer synthesis: an improved traceless linker methodology for aliphatic C-H bond formation. Tetrahedron Lett 1997, 38:977-980.
46. Nelson JC, Young JK, Moore JS: Solid-phase synthesis of phenylacetylene oligomers utilizing a novel 3-propyl-3-(benzyl-supported) triazene linkage. J Org Chem 1996, 61:8160-8168.
47. Lorsbach BA, Miller RB, Kurth MJ: Reissert-based 'traceless' solid-phase synthesis: isoquinoline, and isoxazotine-containing heterocycles. J Org Chem 1996, 61:8716-8717. A novel strategy for traceless synthesis is reported. The Reissert cleavage provides isoquinoline products that bear no evidence of solid-phase synthesis.
48. Bhargava KK, Sarin VK, Trang NL, Cerami A, Merrifield RB: Synthesis of a cyclic analogue of oxidized glutathione by an intersite reaction in a swollen polymer network. J Am Chem Soc 1983, 105:3247-3251.
49. Van Maarseveen JHV, den Hartog JAJ, Engelen V, Finner E, Visser G, Kruse CG: Solid phase ring-closing metathesis: cyclization/cleavage approach towards a seven membered cycloolefin. Tetrahedron Lett 1996, 37:8249-8252.
50. DeWitt SH, Kiely JS, Stankovic CJ, Schroeder MC, Reynolds-Cody DM, Pavia MR: "Diversomers": an approach to nonpeptide, nonoligomeric chemical diversity. Proc Natl Acad Sci USA 1993, 90:6909-6913.
51. Dressman BA, Spangle LA, Kaldor SW: Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization/cleavage step. Tetrahedron Lett 1996, 37:937-940.
52. Hanessian S, Yang RY: Solution and solid phase synthesis of 5-alkoxyhydantoin libraries with a three-fold functional display. Tetrahedron Lett 1996, 37:5835-5838.
53. Scott BO, Siegmund AC, Marlowe CK, Pei Y, Spear KL: Solid phase organic synthesis (SPOS): a novel route to diketopiperazines and diketomorpholines. Mol Divers 1995, 1:125-134.
54. Goodfellow VS, Laudeman CP, Gerrity JI, Burkard M, Strobel E, Zuzack JS, McLeod DA: Rationally designed non-peptides: variously substituted piperazine libraries for the discovery of bradykinin antagonists and other G-protein-coupled receptor ligands. Mol Divers 1996, 2:97-102.
55. Gouilleux L, Fehrentz JA, Winternitz F, Martinez J: Solid phase synthesis of chiral 3-substituted quinazoline-2,4-diones. Tetrahedron Lett 1996, 37:7031-7034.
56. Kolodziej SA, Hamper BC: Solid-phase synthesis of 5,6-dihydropyrimidine-2,4-diones. Tetrahedron Lett 1996, 37:5257-5280.
57. Mayer JP, Zhang J, Bjergarde K, Lenz DM, Gaudino JJ: Solid phase synthesis of 1,4-benzodiazepine-2,5-diones. Tetrahedron Lett 1996, 37:8081-8084.
58. Gordon DW, Steele J: Reductive alkylation on a solid phase: synthesis of a piperazinedione combinatorial library. Bioorg Med Chem Lett 1995, 5:47-50.
59. Virgilio AA, Schürer SC, Ellman JA: Expedient solid-phase synthesis of putative β-turn mimetics incorporating the i + 1, i + 2, and i + 3 sidechains. Tetrahedron Lett 1996, 37:6961-6964.
60. Kaldor SW, Siegel MG, Fritz JE, Dressman BA, Hahn PJ: Use of solid supported nucleophiles and electrophiles for the purification of non-peptide small molecule libraries. Tetrahedron Lett 1996, 37:7193-7196. Support-bound nucleophiles and electrophiles are used to 'quench' excess reactants employed for amine alkylations and acylations performed in solution. Solvent filtration and evaporation provides products in high yield.
61. Gayo LM, Suto MJ: Ion-exchange resins for solution phase parallel synthesis of chemical libraries. Tetrahedron Lett 1997, 38:513-516.
62. Seebach D, Thaler A, Blaser D, Ko SY: 104. Transesterifications with 1,8-diazabicyclo[5.4.0]undec-7-ene/lithium bromide (DBU/LiBr) - also applicable to cleavage of peptides from resins in Merrifield syntheses. Helv Chim Acta 1991, 74:1102-1118.
63. Barn DR, Morphy JR, Rees DC: Synthesis of an array of amides by aluminium chloride assisted cleavage of resin-bound esters. Tetrahedron Lett 1996, 37:3213-3216.
64. Ley SV, Mynett DM, Koot WJ: Solid phase synthesis of bicyclo [2.2.2]octane derivatives via tandem Michael addition reactions and subsequent reductive amination. Synlett 1995:1017-1020.
65. DeGrado WF, Kaiser ET: Polymer-bound oxime esters as supports for solid-phase peptide synthesis. Preparation of protected peptide fragments. J Org Chem 1980, 45:1295-1300.
66. Mohan R, Chou YL. Morrissey MM: Pictet-Spengler reaction on solid support: synthesis of 1,2,3,4-tetrahydro-β-carboline libraries. Tetrahedron Lett 1996, 37:3963-3966.
67. Voyer N, Lavoie A, Pinette M, Bernier J: A convenient solid phase preparation of peptide substituted amides. Tetrahedron Lett 1994, 35:355-358.
68. Kenner GW, McDermott JR, Sheppard RC: The safety catch principle in solid phase synthesis. J Chem Soc Chem Commun 1971:636-637.
69. Backes BJ, Ellman JA: Carbon-carbon bond-forming methods on solid support. Utilization of Kenners 'safety-catch' linker. J Am Chem Soc 1994, 116:11171-11172.
70. Backes BJ, Virgilio AV, Ellman JA: Activation method to prepare a highly reactive acylsulfonamide 'safety-catch' linker for solid-phase synthesis. J Am Chem Soc 1996, 118:3055-3056. Reports an activation method that provides a highly reactive acylsulfonamide for cleavage. Treatment of the activated acylsulfonamide with limiting amounts of nucleophiles provides products in solution without further purification.
71. Gayo LM, Suto MJ: Traceless linker: oxidative activation and displacement of a sulfur-based linker. Tetrahedron Lett 1997, 38:211-214. A sulfur-based linker is described. After an oxidative activation step, limiting amounts of amine nucleophiles can be added to cleave the products from support. Small substituted heterocycles are provided in solution without the need for further purification.
72. Morphy JR, Rankovic Z, Rees DC: A novel linker strategy for solid-phase synthesis. Tetrahedron Lett 1996, 37:3209-3212. A reusable safety-catch linker is reported to prepare 3° amines in high purity.
73. Nielson J, Rasmussen PH: Implementation of a combinatorial cleavage and deprotection scheme. 1, Synthesis of phthalhydrazide libraries. Tetrahedron Lett 1996, 37:3351-3354.
74. Dihn TQ, Armstrong RW: Synthesis of ketones and aldehydes via reactions of Weinreb-type amides on solid support Tetrahedron Lett 1996, 37:1161-1164.
75. Fehrentz JA, Paris M, Heitz A, Velek J, Liu CF, Winternitz F, Martinez J: Improved solid phase synthesis of C-terminal peptide aldehydes. Tetrahedron Lett 1995, 36:7871-7874.
76. Hunt JA, Roush WR: Solid-phase synthesis of 6-deoxyoligosaccharides. J Am Chem Soc 1996, 118:9998-9999.
77. Worster PM, McArthur CR, Leznoff CC: Asymmetric synthesis of 2-alkylcyclohexanones on solid phases. Angew Chem Int Ed 1979, 18:221-222.
78. Moon HS, Schore NE, Kurth MJ: A polymer-supported chiral auxiliary applied to the iodolactonization reaction: preparation of γ-butyrolactones. J Am Chem Soc 1992, 57:6088-6089.
79. 2-symmetric chiral auxiliary: preparation of non-racemic 3,5-disubstituted-γ-butyrolactones. Tetrahedron Lett 1994, 35:8915-8918.
80. Allin SM, Shuttleworth SJ: The preparation and first application of a polymer-supported 'Evans' oxazolidinone. Tetrahedron Lett 1996, 37:8023-8026.
81. Nicolau KC, Winssinger N, Pastor J, DeRoose F: A general and highly efficient solid phase synthesis of oligosaccharides. Total synthesis of a heptasaccharide phytoalexin elicitor (HPE). J Am Chem Soc 1997, 119:449-450.
82. Baldwin JJ, Burbaum JJ, Henderson I, Ohlmeyer MHJ: Synthesis of a small molecule combinatorial library encoded with molecular tags. J Am Chem Soc 1995, 117:5589-5590.
83. Venkatesan H, Greenburg MM: Improved utility of photolabile solid phase synthesis supports for the synthesis of oligonucleotides containing the 3′-hydroxyl termini. J Org Chem 1996, 61:525-529.
84. Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA: Multiple-component condensation strategies for combinatorial chemistry. Accounts Chem Res 1996, 29:123-131.
85. Holmes CP, Jones DG: Reagents for combinatorial organic synthesis: development of a new o-nitrobenzyl photolabile linker for solid phase synthesis. J Org Chem 1995, 60:2318-2319.
86. Ajayaghosh A, Pillai VNR: Solid-phase synthesis and C-terminal amidation of peptides using a photolabile o-nitrobenzhydrylaminopolystyrene support. Tetrahedron Lett 1995, 36:777-780.
87. Brown BB, Wagner DS, Geysen HM: A single-bead decode strategy using electrospray ionization mass spectrometry and a new photolabile linker - 3-amino-3-(2-nitrophenyl)propionic acid. Mol Divers 1995, 1:4-12.
88. Krafft GA, Sutton WR, Cummings RT: Photoactive fluorophores. 3. Synthesis and photoactivation of fluorogenic difunctionalized fluoresceins. J Am Chem Soc 1988, 110:301-303.
89. Routledge A, Abell C, Balasubramanian S: The use of a dithiane protected benzoin photolabile safety catch linker for solid-phase synthesis. Tetrahedron Lett 1997, 38:1227-1230.
90. Salmon SE, Lam KS, Leble M, Kandola A, Khattri PS, Wade S, Pátek M, Kočiš P, Krchňák V, Thorpe D, Felder S: Discovery of biologically active peptides in random libraries: solution-phase testing after staged orthogonal release from resin beads. Proc Natl Acad Sci USA 1993, 90:11708-11712.
91. Kočiš P, Krchňák V, Lebl M: Symmetrical structure allowing the selective multiple release of a defined quantity of peptide from a single bead of polymetric support. Tetrahedron Lett 1993, 34:7251-7252.
92. Cardno M, Bradley M: A simple multiple release system for combinatorial library and peptide analysis. Tetrahedron Lett 1996, 37:135-138.