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Peptide Coupling Reagents, More than a Letter Soup

El-Faham, Ayman, Albericio, Fernando·2011·Chemical Reviews

DOI 10.1021/cr100048w

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ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTPeptide Coupling Reagents, More than a Letter SoupAyman El-Faham*†‡ and Fernando Albericio*†§∥View Author Information† Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain‡ Alexandria University, Faculty of Science, Department of Chemistry, P.O. Box 426, Ibrahimia, 21321 Alexandria, Egypt§ CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain.∥ Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, 08028-Barcelona, SpainE-mail addresses: [email protected]; [email protected]Cite this: Chem. Rev. 2011, 111, 11, 6557–6602Publication Date (Web):August 26, 2011Publication History Received14 February 2010Published online26 August 2011Published inissue 9 November 2011https://pubs.acs.org/doi/10.1021/cr100048whttps://doi.org/10.1021/cr100048wreview-articleACS PublicationsCopyright © 2011 American Chemical SocietyRequest reuse permissionsArticle Views57025Altmetric-Citations906LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Anions,Peptides and proteins,Reaction products,Reagents,Salts Get e-Alerts

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Controlled Microwave Heating in Modern Organic Synthesis
Kappe, C. O. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200400655 · Cited by 3,672
Amide bond formation: beyond the myth of coupling reagents
Valeur, E., & Bradley, M. (2008) · Chemical Society Reviews · doi:10.1039/b701677h · Cited by 2,209
Amide bond formation and peptide coupling
Montalbetti, C., & Falque, V. M. (2005) · Tetrahedron · doi:10.1016/j.tet.2005.08.031 · Cited by 1,879
Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1‐Hydroxy‐benzotriazolen
König, W., & Geiger, R. (1970) · Chemische Berichte · doi:10.1002/cber.19701030319 · Cited by 1,588
1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive
Carpino, L. A. (1993) · Journal of the American Chemical Society · doi:10.1021/ja00063a082 · Cited by 1,513
A New Method of Forming Peptide Bonds
Sheehan, J. C., & Hess, G. P. (1955) · Journal of the American Chemical Society · doi:10.1021/ja01609a099 · Cited by 1,264
The Use of Esters of N-Hydroxysuccinimide in Peptide Synthesis
Anderson, G. W., Zimmerman, J. E., & Callahan, F. M. (1964) · Journal of the American Chemical Society · doi:10.1021/ja01063a037 · Cited by 1,241
Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides
Humphrey, J. M., & Chamberlin, A. R. (1997) · Chemical Reviews · doi:10.1021/cr950005s · Cited by 1,165
New coupling reagents in peptide chemistry
Knorr, R., Trzeciak, A., Bannwarth, W., & Gillessen, D. (1989) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)99616-3 · Cited by 996
Tertiary Phosphane/Tetrachloromethane, a Versatile Reagent for Chlorination, Dehydration, and PN Linkage
Appel, R. (1975) · Angewandte Chemie International Edition in English · doi:10.1002/anie.197508011 · Cited by 944

Show all 300 references

Research works printed but not linked: 53

Elmore D. T., 2002, Amino Acids, Pept., Proteins, 33, 83
Hruby V. J., 1998, Peptide Chemistry, Design and Synthesis of Peptides, Conformational Analysis and Biological Functions
Lloyd-Williams P., 1997, Chemical Approaches to the Synthesis of Peptide and Proteins
Antonovics I., 1967, J. Chem. Soc. (C), 595
Benoiton, N. L.InThe Peptides: Analysis, Synthesis, Biology;Gross, E.; Meienhofer, J., Eds.Academic:New York, 1981; Vol.5, p341.
Orlowska A. J., 1994, Pol. J. Chem., 68, 713
Sabatino, G.; Mulinacci, B.; Alcaro, M. C.; Chelli, M.; Rovero, P.; Papini, A. M.Peptides 2002: Proceedings of the Twenty-Seventh European Peptide Symposium, Aug. 31-Sept. 6, Sorrento, Italy;ESCOM:Leiden, The Netherlands, 2002; p272.
Kent, S. B. H.; Merrifield, R. B.InPeptides 1980: Proceedings of the 16th European Peptide Symposium;Brunfeldt, K., Ed.Scriptor:Copenhagen, 1981; p328.
Albert, J. S.; Hamilton., A. D.InEncyclopedia of Reagents for Organic Synthesis;Paquette, L. A., Ed.Wiley:Chichester, UK, 1995; Vol3, p1751.
Vaughan J. R., 1952, J. Am. Chem. Soc., 74, 676, 10.1021/ja01123a028 · DOI
Meienhofer J., 1979, The Peptides: Analysis, Synthesis, Biology, 1, 263
Bodanszky M., 1979, The Peptides: Analysis, Synthesis, Biology, 105
Jones J. H., 1967, Chem. Commun., 1, 35
Pless, J.InPeptide Synthesis. Peptides, Proceedings of the 5th European Symposium;Oxford Press:Oxford, 1963; p69.
Atherton E., 1988, Tetrahedron, 44, 843, 10.1016/S0040-4020(01)86121-4 · DOI
Kisfaludy, L.; Ceprini, M. Q.; Rakoczy, B.; Kovacs, J.InPeptides 1967: Proceedings of the 8th European Peptide Symposium;Beyerman, H. C.; van de Linde, A.; van den Brink, W. M., Eds.North-Holland:Amsterdam, 1967, p25.
Katritzky A. R., 2009, Arkivoc, 47
Meienhofer J., 1979, The Peptides: Analysis, Synthesis, Biology, 197
For a review of the work on the use of protected amino acid chlorides, see:The Peptides, Methods of Peptide Synthesis;Schröder, E.; Lübke, K., Eds.Academic Press:New York, 1965, p77.
Bergmann M., 1932, Ber. Deutsch. Chem. Ges., 65, 1192, 10.1002/cber.19320650722 · DOI
Crofts P. C., 1963, J. Chem. Soc., 2559
Downie I. M., 1968, Chem. Commun., 1350
Kim Y.-A., 2000, Bull. Korean Chem. Soc., 21, 943
Olah G. A., 1973, Synthesis, 487
Savrda J., 1994, Tetrahedron, 50, 5309, 10.1016/S0040-4020(01)80689-X · DOI
Hudlicky M., 1988, Org. React., 35, 513
Castro B., 1973, Bull. Soc. Chim. Fr., 12, 3359
Castro B., 1977, J. Chem. Res. (S), 7, 182
Wijkmans J. C. H. M., 1994, Recl. Trav. Chim. Pays-Bas., 113, 394
Bofill J. M., 1996, J. Chem. Res. (S), 6, 302
Klose, J.; Henklein, P.; El-Faham, A.; Carpino, L. A.; Bienert, M.InPeptides 1998. Proceedings of the 25th European Peptide Symposium;Bajusz, S.; Hudecz, F., Eds;Akadémiai Kiadó:Budapest, 1999; p204.
Bailén, M. A.; Chinchilla, R.; Dodsworth, D. J.; Nájera, C.; Soriano, J. M.; Yus, M.InPeptides 1998. Proceedings of the 25th European Peptide Symposium;Bajusz, S.; Hudecz, F., Eds;Akadémiai Kiadó:Budapest, 1999; p172.
El-Faham A., 1996, Bull. Fac. Sci., Univ. Alexandria, 36, 73
Panse G. T., 1989, Indian J. Chem., 28, 793
Zhang, D. Y.; Ye, Y. H.Peptide: Biology and Chemistry, Proceedings of the Chinese Peptide Symposium 1990;Du, Y. C., Ed.Science Press:Beijing, China, 1991; p235.
Fan, C. X.; Hao, X. L.; Ye, Y. H.Peptide: Biology and Chemistry, Proceedings of the Chinese Peptide Symposium 1992;Du, Y. C.; Tam, J. P.; Zhang, Y. S., Eds.ESCOM:The Netherlands, 1993; p297.
Kokare N. D., 2007, Synthesis, 5, 766
Li P., 2001, J. Pept. Res., 58, 129, 10.1034/j.1399-3011.2001.00867.x · DOI
Fan C.-X., 1986, Synth. Commun., 26, 1455, 10.1080/00397919608003508 · DOI
Jackson A. G., 1976, Tetrahedron Lett., 17, 3627, 10.1016/S0040-4039(00)92978-2 · DOI
Devedas B., 1978, Indian J. Chem., 16, 1026
Kundu B., 1989, Indian J. Chem., 28, 604
Topuzzan N. O., 1991, J. Org. Chem. (USSR), 27, 2148
Kundu B., 1996, J. Chem. Res., Synop., 4, 200
Itoh M., 1974, Tetrahedron Lett., 15, 3089, 10.1016/S0040-4039(01)91831-3 · DOI
Jastrzabek K., 2007, J. Int. J. Pept. Res. Ther., 13, 229, 10.1007/s10989-006-9071-y · DOI
Kalir R., 1975, Eur. J. Biochem., 59, 55, 10.1111/j.1432-1033.1975.tb02424.x · DOI
Valeur E., 2007, Tetrahedron, 63, 8855, 10.1016/j.tet.2007.06.019 · DOI
Blodgett, J. K.; Brammeier, N. M.; Califano, J. C.; Devin, C.; Tolle, C.Presented at the 16th American Peptide Symposium, Minneapolis, MN 1999, June 26–July 1, poster c 039.
Gadhwal S., 1998, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 37, 725
El’tsov A. V., 1995, Zh. Obshch. Khim., 65, 511
Hajipour A. R., 2001, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 40, 504
Jou G., 1997, J. Org. Chem., 62, 354, 10.1021/jo961932h · DOI

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Authors: El-Faham, A., & Albericio, F.
Affiliations: Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain
Venue: Chemical Reviews
Publisher: American Chemical Society (ACS)
Published: 2011-08-26
Volume: 111
Issue: 11
Pages: 6557-6602
ISSN: 0009-2665 (ISSN-L)
1520-6890
DOI: 10.1021/cr100048w
OpenAlex: W2041513075
Cited by: 1,245
References: 300
Citations by year: 2026: 81 · 2025: 88 · 2024: 117 · 2023: 93 · 2022: 96 · 2021: 114 · 2020: 90 · 2019: 95 · 2018: 92 · 2017: 71 · 2016: 68 · 2015: 74 · 2014: 73 · 2013: 61 · 2012: 28
FWCI: 4.74
Type: journal article
Language: en
Open access: closed
Locations: Chemical Reviews (publishedVersion)
PubMed (publishedVersion)
Topics: Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Analysis
Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biochemical and Structural Characterization
Keywords: peptide coupling reagents, peptide synthesis, peptide bond formation, protecting groups, protecting group chemistry, peptide synthesis reagents, peptide functionalization, peptide purification
MeSH terms: Indicators and Reagents, Peptides

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Peptide Coupling Reagents, More than a Letter Soup

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