Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 3
Submit an article Journal homepage
319
Views
47
CrossRef citations to date
0
Altmetric
Original Articles

Comparative Study of Selected Coupling Reagents in Dipeptide Synthesis

Joseph Dudash Jr. Department of Chemistry, University of Pennsylvania Philadelphia, PA 19104-6323; Department of Chemistry, Stanford University, Stanford, CA, 94305
,
Jianjun Jiang Department of Chemistry, University of Pennsylvania Philadelphia, PA 19104-6323
,
Scott C. Mayer Department of Chemistry, University of Pennsylvania Philadelphia, PA 19104-6323
&
Madeleine M. Joullié Department of Chemistry, University of Pennsylvania Philadelphia, PA 19104-6323
Pages 349-356 | Received 18 Aug 1992, Published online: 23 Sep 2006

Citations (47)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (3)

MadathilB. Gopinathan, Chunyang Jin & KennethS. Rehder. (2009) Synthesis of Carnosine-d7 and Anserine-d4 for Use as Internal Standards in Liquid Chromatography–Mass Spectrometry. Synthetic Communications 39:22, pages 3973-3981.
Read now
Fernando Albeiicio, Rafael Chinchilla, DavidJ. Dodsworth & Carmen Nájera. (2001) NEW TRENDS IN PEPTIDE COUPLING REAGENTS. Organic Preparations and Procedures International 33:3, pages 203-303.
Read now
Jianjun Jiang, Wen-Ren Li & MadeleineM. Joullié. (1994) Selective Removal of Fluorenylmethoxycarbonyl (FMOC) Groups Under Mild Conditions. Synthetic Communications 24:2, pages 187-195.
Read now

Articles from other publishers (44)

Mirela Matić, Bernard Denegri, Ivana Tarandek & Lu Turković. (2022) Nucleofugality of diphenylphosphinate and kinetic stabilities of secondary and tertiary benzylic diphenylphosphinates in aqueous solvents. International Journal of Chemical Kinetics 54:10, pages 561-569.
Crossref
Yingying Cheng, Shoubin Tang, Yian Guo & Tao Ye. (2018) Total Synthesis of Anti-tuberculosis Natural Products Ilamycins E 1 and F . Organic Letters 20:19, pages 6166-6169.
Crossref
Tyler K. Allred, Francesco Manoni & Patrick G. Harran. (2017) Exploring the Boundaries of “Practical”: De Novo Syntheses of Complex Natural Product-Based Drug Candidates. Chemical Reviews 117:18, pages 11994-12051.
Crossref
Clare E. Gutteridge, Joshua W. Major, Daniel A. Nin, Sean M. Curtis, Apurba K. Bhattacharjee, Lucia Gerena & Daniel A. Nichols. (2016) In vitro efficacy of 2,N-bisarylated 2-ethoxyacetamides against Plasmodium falciparum. Bioorganic & Medicinal Chemistry Letters 26:3, pages 1048-1051.
Crossref
Gwénaël Forcher, Andrew Silvanus, Pierre de Frémont, Béatrice Jacques, Morwenna S.M. Pearson-Long, Fabien Boeda & Philippe Bertus. (2015) A stereoselective access to a ferrocene-based planar chiral triazolium salt. Journal of Organometallic Chemistry 797, pages 1-7.
Crossref
Valentine I. Vullev & Vicente Nuñez. 2015. Encyclopedia of Surface and Colloid Science, Third Edition. Encyclopedia of Surface and Colloid Science, Third Edition 1 22 .
Nakia Maulucci, Maria Giovanna Chini, Simone Di Micco, Irene Izzo, Emiddio Cafaro, Adele Russo, Paola Gallinari, Chantal Paolini, Maria Chiara Nardi, Agostino Casapullo, Raffaele Riccio, Giuseppe Bifulco & Francesco De Riccardis. (2007) Molecular Insights into Azumamide E Histone Deacetylases Inhibitory Activity. Journal of the American Chemical Society 129:10, pages 3007-3012.
Crossref
Dennis N. Kevill & Han Joong Koh. (2007) Correlation of the rates of solvolysis of diphenylphosphinyl chloride using an extended form of the Grunwald–Winstein equation. Journal of Physical Organic Chemistry 20:2, pages 88-92.
Crossref
Irene Izzo, Nakia Maulucci, Giuseppe Bifulco & Francesco De Riccardis. (2006) Total Synthesis of Azumamides A and E. Angewandte Chemie International Edition 45:45, pages 7557-7560.
Crossref
Irene Izzo, Nakia Maulucci, Giuseppe Bifulco & Francesco De Riccardis. (2006) Total Synthesis of Azumamides A and E. Angewandte Chemie 118:45, pages 7719-7722.
Crossref
Kristin N. Barlett, Robert V. Kolakowski, Sreenivas Katukojvala & Lawrence J. Williams. (2006) Thio Acid/Azide Amidation:  An Improved Route to N -Acyl Sulfonamides . Organic Letters 8:5, pages 823-826.
Crossref
Paulo F. Santos, Natarajan Srinivasan, Paulo S. Almeida, Ana M. Lobo & Sundaresan Prabhakar. (2005) A formal synthesis of (±)-physostigmine via 3,3-rearrangement of a bis-enamine. Tetrahedron 61:38, pages 9147-9156.
Crossref
Hamdy M. Abdel‐Rahman, Nawal A. El‐Koussi, Gamal S. Alkaramany, Adel F. Youssef & Yoshiaki Kiso. (2004) A Novel Dipeptide‐based HIV Protease Inhibitor Containing Allophenylnorstatine. Archiv der Pharmazie 337:11, pages 587-598.
Crossref
Csaba Wéber, Attila Bielik, Györgyi I. Szendrei, György M. Keserû & István Greiner. (2004) Solid-phase synthesis of an N -(phenylalkyl)cinnamide library via Horner–Wadsworth–Emmons reaction. Bioorganic & Medicinal Chemistry Letters 14:5, pages 1279-1281.
Crossref
Louis A. Carpino, Jusong Xia, Chongwu Zhang & Ayman El-Faham. (2003) Organophosphorus and Nitro-Substituted Sulfonate Esters of 1-Hydroxy-7-azabenzotriazole as Highly Efficient Fast-Acting Peptide Coupling Reagents. The Journal of Organic Chemistry 69:1, pages 62-71.
Crossref
Apurva Chaudhary, Michael Girgis, Mahavir Prashad, Bin Hu, Denis Har, Oljan Repič & Thomas J. Blacklock. (2003) Using mixed anhydrides from amino acids and isobutyl chloroformate in N-acylations: a case study on the elucidation of mechanism of urethane formation and starting amino acid liberation using carbon dioxide as the probe. Tetrahedron Letters 44:29, pages 5543-5546.
Crossref
Fumiaki Yokokawa & Takayuki Shioiri. (2002) Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide. Tetrahedron Letters 43:48, pages 8673-8677.
Crossref
Fumiaki Yokokawa, Hirofumi Sameshima, Daichi Katagiri, Toyohiko Aoyama & Takayuki Shioiri. (2002) Total syntheses of lyngbyabellins A and B, potent cytotoxic lipopeptides from the marine cyanobacterium Lyngbya majuscula. Tetrahedron 58:46, pages 9445-9458.
Crossref
Tao Hu & James S. Panek. (2002) Enantioselective Synthesis of the Protein Phosphatase Inhibitor (−)-Motuporin. Journal of the American Chemical Society 124:38, pages 11368-11378.
Crossref
Fumiaki Yokokawa, Hirofumi Sameshima, Yasuko In, Katsuhiko Minoura, Toshimasa Ishida & Takayuki Shioiri. (2002) Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin. Tetrahedron 58:40, pages 8127-8143.
Crossref
Glen W. Spears, Kiyoshi Tsuji, Takashi Tojo, Hiroaki Nishimura & Takashi Ogino. (2009) An efficient synthesis of a class of novel N ‐Alkyl‐ N ‐aryl‐4‐hydroxy‐1‐methyl‐2‐oxo‐1,2‐dihydro‐3‐quinolinecarbothioamides . Journal of Heterocyclic Chemistry 39:4, pages 799-804.
Crossref
Marcus A. Tius. (2002) Synthesis of the cryptophycins. Tetrahedron 58:22, pages 4343-4367.
Crossref
Michael S. Leonard & Madeleine M. Joullié. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Sopheak Son & Betty A. Lewis. (2001) Free Radical Scavenging and Antioxidative Activity of Caffeic Acid Amide and Ester Analogues:  Structure−Activity Relationship. Journal of Agricultural and Food Chemistry 50:3, pages 468-472.
Crossref
Fumiaki Yokokawa, Akiko Inaizumi & Takayuki Shioiri. (2001) Synthetic studies of micropeptin T-20, a novel 3-amino-6-hydroxy-2-piperidone (Ahp)-containing cyclic depsipeptide. Tetrahedron Letters 42:34, pages 5903-5908.
Crossref
Claudio Palomo, Jesus M. Aizpurua, Iraida Loinaz, Maria Jose Fernandez-Berridi & Lourdes Irusta. (2001) Scavenging of Fluorinated N , N ‘ -Dialkylureas by Hydrogen Binding:  A Novel Separation Method for Fluorous Synthesis . Organic Letters 3:15, pages 2361-2364.
Crossref
Fumiaki Yokokawa, Hirofumi Sameshima & Takayuki Shioiri. (2001) Total synthesis of lyngbyabellin A, a potent cytotoxic metabolite from the marine cyanobacterium Lyngbya majuscula. Tetrahedron Letters 42:25, pages 4171-4174.
Crossref
Arkadiusz Kłys, Ryszard B Nazarski & Janusz Zakrzewski. (2001) Diastereomeric amides from rac-3,3′,4,4′-tetramethyl-1,1′-diphosphaferrocene-2-carboxylic acid and (S)-α-phenylethylamine: separation and determination of absolute configuration. Journal of Organometallic Chemistry 627:2, pages 135-138.
Crossref
Takeshi Kitahara & Wataru Kuriyama. (2001) Synthesis of Apicidin. HETEROCYCLES 55:1, pages 1.
Crossref
Amy M. Elder & Daniel H. Rich. (1999) Two Syntheses of the 16- and 17-Membered DEF Ring Systems of Chloropeptin and Complestatin. Organic Letters 1:9, pages 1443-1446.
Crossref
Wen-Chung Shieh, John A. Carlson & Michael E. Shore. (1999) A novel kinetically-controlled peptide synthesis—Dramatic increase of chemical yield with retention of chiral integrity. Tetrahedron Letters 40:40, pages 7167-7170.
Crossref
Michael S. Hemenway & Horacio F. Olivo. (1999) Syntheses of New Phosphorus-Containing Azabicycloalkanes and Their Microbial Hydroxylation Using Beauveria bassiana . The Journal of Organic Chemistry 64:17, pages 6312-6318.
Crossref
Raghu Samy, Hong Yong Kim, Matthew Brady & Peter L. Toogood. (1999) Total Synthesis of Motuporin and 5-[ l -Ala]-Motuporin . The Journal of Organic Chemistry 64:8, pages 2711-2728.
Crossref
Peter Wipf. 1998. 187 228 .
Andreas Jakobs, Jean Bernadou & Bernard Meunier. (1997) Preparation of Tetracationic Metalloporphyrin−Spermine Conjugates. The Journal of Organic Chemistry 62:11, pages 3505-3510.
Crossref
Lin-hua Zhang, J. C. Chung, T. D. Costello, I. Valvis, P. Ma, S. Kauffman & R. Ward. (1997) The Enantiospecific Synthesis of an Isoxazoline. A RGD Mimic Platelet GPIIb/IIIa Antagonist. The Journal of Organic Chemistry 62:8, pages 2466-2470.
Crossref
Holger Wagner, Klaus Harms, Ulrich Koert, Sabine Meder & Günther Boheim. (2003) Oligo‐THF Peptides: Synthesis, Membrane Insertion, and Studies of Ion Channel Activity. Angewandte Chemie International Edition in English 35:22, pages 2643-2646.
Crossref
Holger Wagner, Klaus Harms, Ulrich Koert, Sabine Meder & Günther Boheim. (2006) Oligo‐THF‐Peptide: Synthese, Membraneinbau und Untersuchungen zur Ionenkanalaktivität. Angewandte Chemie 108:22, pages 2836-2839.
Crossref
Deng Jingen, Hamada Yasumasa & Shioiri Takayuki. (1996) A new synthesis of cyclotheonamide B via guanidination of ornithine. Tetrahedron Letters 37:13, pages 2261-2264.
Crossref
Peter Wipf & Paul C. Fritch. (1996) Total Synthesis and Assignment of Configuration of Lissoclinamide 7. Journal of the American Chemical Society 118:49, pages 12358-12367.
Crossref
Christopher D.J. Boden & Gerald Pattenden. (1995) Cyclopeptides from ascidians. Total synthesis of lissoclinamide 4, and a general strategy for the synthesis of chiral thiazoline-containing macrocyclic peptides. Tetrahedron Letters 36:34, pages 6153-6156.
Crossref
Jingen Deng, Yasumasa Hamada, Takayuki Shioiri, Shigeki Matsunaga & Nobuhiro Fusetani. (2003) Synthesis of Cyclotheonamide B and Its Derivatives. Angewandte Chemie International Edition in English 33:17, pages 1729-1731.
Crossref
Jingen Deng, Yasumasa Hamada, Takayuki Shioiri, Shigeki Matsunaga & Nobuhiro Fusetani. (2006) Synthese von Cyclotheonamid B und Derivaten. Angewandte Chemie 106:17, pages 1811-1813.
Crossref
J. JUN. DUDASH, J. JIANG, S. C. MAYER & M. M. JOULLIE. (2010) ChemInform Abstract: Comparative Study of Selected Coupling Reagents in Dipeptide Synthesis.. ChemInform 24:32.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.