Linkers and Cleavage Strategies in Solid-Phase Organic Synthesis and Combinatorial Chemistry

Solid Phase Peptide Synthesis. I. The Synthesis of a Tetrapeptide

Merrifield, R. B. (1963) · Journal of the American Chemical Society · doi:10.1021/ja00897a025 · Cited by 7,647

Solid phase peptide synthesis utilizing 9‐fluorenylmethoxycarbonyl amino acids

FIELDS, G. B., & NOBLE, R. L. (1990) · International Journal of Peptide and Protein Research · doi:10.1111/j.1399-3011.1990.tb00939.x · Cited by 2,493

Use of peptide synthesis to probe viral antigens for epitopes to a resolution of a single amino acid.

Geysen, H. M., Meloen, R. H., & Barteling, S. J. (1984) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.81.13.3998 · Cited by 1,475

Synthesis and Applications of Small Molecule Libraries

Thompson, L. A., & Ellman, J. A. (1996) · Chemical Reviews · doi:10.1021/cr9402081 · Cited by 1,452

Encoded combinatorial chemistry.

Brenner, S., & Lerner, R. A. (1992) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.89.12.5381 · Cited by 1,014

Application of the Principle of Hard and Soft Acids and Bases to Organic Chemistry

Pearson, R. G., & Songstad, J. (1967) · Journal of the American Chemical Society · doi:10.1021/ja00984a014 · Cited by 906

Solid-phase synthesis of protected peptide fragments using a trialkoxy-diphenyl-methylester resin.

Rink, H. (1987) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)96384-6 · Cited by 857

Combinatorial Synthesis of Small Organic Molecules

Balkenhohl, F., von dem Bussche‐Hünnefeld, C., Lansky, A., & Zechel, C. (1996) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199622881 · Cited by 726

A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesis

KING, D. S., FIELDS, C. G., & FIELDS, G. B. (1990) · International Journal of Peptide and Protein Research · doi:10.1111/j.1399-3011.1990.tb00976.x · Cited by 725

New rules of selectivity: allylic alkylations catalyzed by palladium

Trost, B. M. (1980) · Accounts of Chemical Research · doi:10.1021/ar50155a001 · Cited by 635

Solid-Phase Peptide Synthesis. III. An Improved Synthesis of Bradykinin*

Merrifield, R. B. (1964) · Biochemistry · doi:10.1021/bi00897a032 · Cited by 572

An SN2 deprotection of synthetic peptides with a low concentration of hydrofluoric acid in dimethyl sulfide: evidence and application in peptide synthesis

Tam, J. P., Heath, W. F., & Merrifield, R. B. (1983) · Journal of the American Chemical Society · doi:10.1021/ja00359a014 · Cited by 545

Complex synthetic chemical libraries indexed with molecular tags.

Ohlmeyer, M. H., Swanson, R. N., Dillard, L. W., Reader, J. C., Asouline, G., Kobayashi, R., Wigler, M., & Still, W. C. (1993) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.90.23.10922 · Cited by 445

2‐Chlorotrityl chloride resin: Studies on anchoring of Fmoc‐amino acids and peptide cleavage

CHATZI, K. B. O., GATOS, D., & STAVROPOULOS, G. (1991) · International Journal of Peptide and Protein Research · doi:10.1111/j.1399-3011.1991.tb00769.x · Cited by 407

Bromination and lithiation: two important steps in the functionalization of polystyrene resins

Farrall, M. J., & Frechet, J. M. J. (1976) · The Journal of Organic Chemistry · doi:10.1021/jo00886a023 · Cited by 350

Towards the Chemical Synthesis of Proteins

Bayer, E. (1991) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199101133 · Cited by 347

Pega: a flow stable polyethylene glycol dimethyl acrylamide copolymer for solid phase synthesis.

Meldal, M. (1992) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)79604-3 · Cited by 342

"Diversomers": an approach to nonpeptide, nonoligomeric chemical diversity.

DeWitt, S. H., Kiely, J. S., Stankovic, C. J., Schroeder, M. C., Cody, D. M., & Pavia, M. R. (1993) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.90.15.6909 · Cited by 340

Preparation and application of the 5-(4-(9-fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for the solid-phase synthesis of C-terminal peptide amides under mild conditions

Albericio, F., Kneib-Cordonier, N., Biancalana, S., Gera, L., Masada, R. I., Hudson, D., & Barany, G. (1990) · The Journal of Organic Chemistry · doi:10.1021/jo00299a011 · Cited by 327

A new synthetic route to tert-butyloxycarbonylaminoacyl-4-(oxymethyl)phenylacetamidomethyl-resin, an improved support for solid-phase peptide synthesis

Mitchell, A. R., Kent, S. B. H., Engelhard, M., & Merrifield, R. B. (1978) · The Journal of Organic Chemistry · doi:10.1021/jo00408a022 · Cited by 326

Darstellung geschützter peptid-fragmente unter einsatz substituierter triphenylmethyl-harze

Barlos, K., Gatos, D., Kallitsis, J. K., Papaphotiu, G., Sotiriu, P., Wenqing, Y., & Schäfer, W. (1989) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)99290-6 · Cited by 305

Discovery of Sequence-Selective Peptide Binding by Synthetic Receptors Using Encoded Combinatorial Libraries

Still, W. C. (1996) · Accounts of Chemical Research · doi:10.1021/ar950166i · Cited by 305

The Synthesis of Ribonuclease A

Gutte, B., & Merrifield, R. B. (1971) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)62396-8 · Cited by 303

Solid-phase synthesis of oligosaccharides. I. Preparation of the solid support. Poly[p-(1-propen-3-ol-1-yl)styrene]

Schuerch, C., & Frechet, J. M. (1971) · Journal of the American Chemical Society · doi:10.1021/ja00731a031 · Cited by 285

Backbone Amide Linker (BAL) Strategy for Solid-Phase Synthesis of C-Terminal-Modified and Cyclic Peptides1,2,3

Jensen, K. J., Alsina, J., Songster, M. F., Vágner, J., Albericio, F., & Barany, G. (1998) · Journal of the American Chemical Society · doi:10.1021/ja974116f · Cited by 277

The safety catch principle in solid phase peptide synthesis

Kenner, G. W., McDermott, J. R., & Sheppard, R. C. (1971) · Journal of the Chemical Society D: Chemical Communications · doi:10.1039/c29710000636 · Cited by 262

Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage

Holmes, C. P. (1997) · The Journal of Organic Chemistry · doi:10.1021/jo961602x · Cited by 254

Activation Method to Prepare a Highly Reactive Acylsulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis1

Backes, B. J., Virgilio, A. A., & Ellman, J. A. (1996) · Journal of the American Chemical Society · doi:10.1021/ja9535165 · Cited by 253

tert-Butoxycarbonylaminoacyl-4-(oxymethyl)phenylacetamidomethyl-resin, a more acid-resistant support for solid-phase peptide synthesis

Mitchell, A. R., Erickson, B. W., Ryabtsev, M. N., Hodges, R. S., & Merrifield, R. B. (1976) · Journal of the American Chemical Society · doi:10.1021/ja00439a041 · Cited by 249

A General and Highly Efficient Solid Phase Synthesis of Oligosaccharides. Total Synthesis of a Heptasaccharide Phytoalexin Elicitor (HPE)

Nicolaou, K. C., Winssinger, N., Pastor, J., & DeRoose, F. (1997) · Journal of the American Chemical Society · doi:10.1021/ja963482g · Cited by 229

Generation and screening of combinatorial peptide libraries designed for rapid sequencing by mass spectrometry

Youngquist, R. S., Fuentes, G. R., Lacey, M. P., & Keough, T. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00119a002 · Cited by 219

Carboxyl-catalyzed intramolecular aminolysis. Side reaction in solid-phase peptide synthesis

Gisin, B. F., & Merrifield, R. B. (1972) · Journal of the American Chemical Society · doi:10.1021/ja00764a036 · Cited by 217

Reagents for Combinatorial Organic Synthesis: Development of a New o-Nitrobenzyl Photolabile Linker for Solid Phase Synthesis

Holmes, C. P., & Jones, D. G. (1995) · The Journal of Organic Chemistry · doi:10.1021/jo00113a004 · Cited by 211

An Alkanesulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis

Backes, B. J., & Ellman, J. A. (1999) · The Journal of Organic Chemistry · doi:10.1021/jo981990y · Cited by 203

Convergent solid-phase peptide synthesis

Lloyd-Williams, P., Albericio, F., & Giralt, E. (1993) · Tetrahedron · doi:10.1016/s0040-4020(01)81800-7 · Cited by 203

Peptide synthesis. Part 8. A system for solid-phase synthesis under low pressure continuous flow conditions

Dryland, A., & Sheppard, R. C. (1986) · Journal of the Chemical Society, Perkin Transactions 1 · doi:10.1039/p19860000125 · Cited by 192

Use of Ilydrogen Fluoride in Merrifield Solid-Phase Peptide Synthesis

Lenard, J., & Robinson, A. B. (1967) · Journal of the American Chemical Society · doi:10.1021/ja00977a057 · Cited by 167

Popcorn Polymer as a Support in Multistep Syntheses

Letsinger, R. L., & Kornet, M. J. (1963) · Journal of the American Chemical Society · doi:10.1021/ja00902a054 · Cited by 161

Designed Epothilones: Combinatorial Synthesis, Tubulin Assembly Properties, abd Cytotoxic Action against Taxol‐Resistant Tumor Cells

Nicolaou, K. C., Vourloumis, D., Li, T., Pastor, J., Winssinger, N., He, Y., Ninkovic, S., Sarabia, F., Vallberg, H., Roschangar, F., et al. (1997) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199720971 · Cited by 148

Major Simplifications in Oligosaccharide Syntheses Arising from a Solid-Phase Based Method: An Application to the Synthesis of the Lewis b Antigen

Randolph, J. T., McClure, K. F., & Danishefsky, S. J. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00126a012 · Cited by 140

A New Method for Releasing Oxytocin from Fully-protected Nona-peptides Using Anhydrous Hydrogen Fluoride

Sakakibara, S., & Shimonishi, Y. (1965) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.38.1412 · Cited by 139

Solid and Solution Phase Synthesis and Biological Evaluation of Combinatorial Sarcodictyin Libraries

Nicolaou, K. C., Winssinger, N., Vourloumis, D., Ohshima, T., Kim, S., Pfefferkorn, J. A., Xu, J.-Y., & Li, T. (1998) · Journal of the American Chemical Society · doi:10.1021/ja9823870 · Cited by 132

The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols

Fyles, T. M., & Leznoff, C. C. (1976) · Canadian Journal of Chemistry · doi:10.1139/v76-135 · Cited by 125

Development of a Novel Silyl Ether Linker for Solid-Phase Organic Synthesis1

Boehm, T. L., & Showalter, H. D. (1996) · The Journal of Organic Chemistry · doi:10.1021/jo961242d · Cited by 120

Solid Phase Synthesis of Peptides and Glycopeptides on Polymeric Supports with Allylic Anchor Groups

Kunz, H., & Dombo, B. (1988) · Angewandte Chemie International Edition in English · doi:10.1002/anie.198807111 · Cited by 119

Synthesis of ‘head-to-tail’ cyclized peptides on solid support by Fmoc chemistry

Trzeciak, A., & Bannwarth, W. (1992) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)61311-4 · Cited by 112

An improved polystyrene support for solid phase peptide synthesis

Sparrow, J. T. (1976) · The Journal of Organic Chemistry · doi:10.1021/jo00870a013 · Cited by 111

Tagged versus untagged libraries: methods for the generation and screening of combinatorial chemical libraries.

Janda, K. D. (1994) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.91.23.10779 · Cited by 106

Discovery of biologically active peptides in random libraries: solution-phase testing after staged orthogonal release from resin beads.

Salmon, S. E., Lam, K. S., Lebl, M., Kandola, A., Khattri, P. S., Wade, S., Pátek, M., Kocis, P., Krchňák, V., & Thorpe, D. (1993) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.90.24.11708 · Cited by 100

Azide solid phase peptide synthesis

Felix, A. M., & Merrifield, R. B. (1970) · Journal of the American Chemical Society · doi:10.1021/ja00708a046 · Cited by 91

A paradigm for drug discovery employing encoded combinatorial libraries.

Burbaum, J. J., Ohlmeyer, M. H. J., Reader, J. C., Henderson, I. M., Dillard, L. W., Li, G., Randle, T. L., SIGAL, N. H., Chelsky, D., & Baldwin, J. J. (1995) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.92.13.6027 · Cited by 90

Fischer indole synthesis on a solid support

Hutchins, S. M., & Chapman, K. T. (1996) · Tetrahedron Letters · doi:10.1016/0040-4039(96)00997-5 · Cited by 90

Preparation of aminomethyl-polystyrene resin by direct amidomethylation

Mitchell, A. R., Kent, S. B. H., Erickson, B. W., & Merrifield, R. B. (1976) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)93112-5 · Cited by 86

Solid phase synthesis of chiral 3-substituted quinazoline-2,4-diones

Gouilleux, L., Fehrentz, J., Winternitz, F., & Martínez, J. (1996) · Tetrahedron Letters · doi:10.1016/0040-4039(96)01541-9 · Cited by 85

Lactone and Lactam Library Synthesis by Silver Ion-Assisted Orthogonal Cyclization of Unprotected Peptides

Zhang, L., & Tam, J. P. (1999) · Journal of the American Chemical Society · doi:10.1021/ja983859d · Cited by 84

New segment-coupling method for peptide synthesis in aqueous solution: application to synthesis of human [Gly17]-beta-endorphin.

Blake, J., & Li, C. H. (1981) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.78.7.4055 · Cited by 80

Improved approach for anchoring N α‐9‐fluorenylmethyloxycarbonylamino acids as p ‐alkoxybenzyl esters in solid‐phase peptide synthesis

Alberício, F., & Bárány, G. (1985) · International journal of peptide & protein research · doi:10.1111/j.1399-3011.1985.tb03182.x · Cited by 80

Creation and functional screening of a multi-usepeptide library.

Jayawickreme, C. K., Graminski, G. F., Quillan, J. M., & Lerner, M. R. (1994) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.91.5.1614 · Cited by 73

Practical approach to solid‐phase synthesis of C‐terminal peptide amides under mild conditions based on a photolysable anchoring linkage1

Hammer, R. P., Alberício, F., Gera, L., & Bárány, G. (1990) · International journal of peptide & protein research · doi:10.1111/j.1399-3011.1990.tb00081.x · Cited by 70

Synthesis of deaminooxytocin by the solid phase method

Takashima, H., du Vigneaud, V., & Merrifield, R. B. (1968) · Journal of the American Chemical Society · doi:10.1021/ja01007a038 · Cited by 66

Cyclisation/cleavage of macrocycles by ring-closing metathesis on solid support—conformational studies

Pernerstorfer, J. (1997) · Chemical Communications · doi:10.1039/a704976e · Cited by 66

Microchemical structural determination of a peptoid covalently bound to a polymeric bead by matrix-assisted laser desorption ionization time-of-flight mass spectrometry

Zambias, R. A., Boulton, D. A., & Griffin, P. R. (1994) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)73334-x · Cited by 58

A novel thioether linker: Chemical synthesis of a HIV-1 protease analogue by thioether ligation

Englebretsen, D. R., Garnham, B., Bergman, D. A., et al. (1995) · Tetrahedron Letters · doi:10.1016/0040-4039(95)01843-7 · Cited by 54

Solid-phase synthesis of peptides using allylic anchoring groups. An investigation of their palladium-catalysed cleavage

Lloyd‐Williams, P., Jou, G., Alberício, F., & Giralt, E. (1991) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)79906-0 · Cited by 52

Active carbonate resins: Application to the solid-phase synthesis of alcohol, carbamate and cyclic peptides

Alsina, J., Rabanal, F., Chiva, C., Giralt, E., & Alberício, F. (1998) · Tetrahedron · doi:10.1016/s0040-4020(98)00606-1 · Cited by 49

Screening an Inverted Peptide Library in Water with a Guanidinium-Based Tweezer Receptor

Davies, M., Bonnat, M., Guillier, F., Kilburn, J., & Bradley, M. (1998) · The Journal of Organic Chemistry · doi:10.1021/jo981741+ · Cited by 45

A Redox-Sensitive Resin Linker for the Solid Phase Synthesis of C-Terminal Modified Peptides

Zheng, A., Shan, D., & Wang, B. (1998) · The Journal of Organic Chemistry · doi:10.1021/jo981528d · Cited by 45

Solid phase synthesis of 1-aminohydantoin libraries

Wilson, L. J., Li, M., & Portlock, D. E. (1998) · Tetrahedron Letters · doi:10.1016/s0040-4039(98)01009-0 · Cited by 44

Library generation through successive substitution of trichlorotriazine

Staňková, M., & Lebl, M. (1996) · Molecular Diversity · doi:10.1007/bf01718703 · Cited by 40

A novel linker for the attachment of alcohols to solid supports

Böhm, G., Dowden, J., Rice, D. C., et al. (1998) · Tetrahedron Letters · doi:10.1016/s0040-4039(98)00593-0 · Cited by 34

Synthetic combinatorial libraries: Views on techniques and their application

Madden, D., Krchňák, V., & Lebl, M. (1995) · Perspectives in Drug Discovery and Design · doi:10.1007/bf02172067 · Cited by 33

A new linker for the synthesis of C-terminal peptide α-oxo-aldehydes

Fruchart, J.-S., Gras‐Masse, H., & Melnyk, O. (1999) · Tetrahedron Letters · doi:10.1016/s0040-4039(99)01161-2 · Cited by 32

Binary Encoding of Compound Libraries

Eckes, P. (1994) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199415731 · Cited by 25

Preparation of peptide thioacids using the Kaiser oxime resin

Schwabacher, A. W., & Maynard, T. L. (1993) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)91771-4 · Cited by 24

Solid Phase Synthesis of Peptides with Carboxyl‐Terminal Amides—Thyrotropin‐Releasing Factor (TRF)

Gross, E., Nöda, K., & NISULA, B. C. (1973) · Angewandte Chemie International Edition in English · doi:10.1002/anie.197306641 · Cited by 21

A Reductive Acidolysis Final Deprotection Strategy in Solid Phase Peptide Synthesis Based on Safety-Catch Protection.

Kimura, T., FUKUI, T., Tanaka, S., et al. (1997) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.45.18 · Cited by 17

Rational design of functional and tunable oscillating enzymatic networks

Semenov, S. N., Wong, A. S. Y., van der Made, R. M., Postma, S. G. J., Groen, J., van Roekel, H. W. H., de Greef, T. F. A., & Huck, W. T. S. (2015) · Nature Chemistry · doi:10.1038/nchem.2142 · Cited by 285