New Trends in Peptide Coupling Reagents

Albeiicio, Fernando; Chinchílla, Rafael; Dodsworth, David J.; Nájera, Carmén

doi:10.1080/00304940109356592

Cited by 131 publications

(42 citation statements)

References 360 publications

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“…Crude diamine 75 was subjected to several coupling reagents, 46 including (but not limited to) HATU, HBTU, TCTU, DPPA, T3P, EDC, DIC, DCC, BOP, BOP-Cl, PyAOP, PyBOP, PyBrOP, and cyanuric chloride in several combinations of polar solvents ( 75 was only soluble in DMF, DMSO, and water in solvent screens). Interestingly, base seemed to inhibit thes reaction (and eventually cause decomposition).…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

et al. 2011

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Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau’amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. Next, the enantioselective synthesis of the chlorocyclopentane core featuring a scalable, catalytic, enantioselective Diels–Alder reaction of a 1-siloxydiene is outlined in detail. Finally, the successful divergent conversion of this core to each of the aforementioned natural products, and the ensuing methodological developments are described.

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Section: Resultsmentioning

confidence: 99%

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

et al. 2011

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“…For the incorporation of each amino acid, the carboxyl function must be activated. This is performed by using carbodiimides in the presence of N-hydroxybenzotriazoles or stand-up coupling reagents, such as uronium/aminium or phosphonium salts [41]. After coupling, the extent of the coupling is verified by a colorimetric test, the ninhydrin test being the most convenient.…”

Section: Peptide Synthesismentioning

confidence: 99%

Peptides and Metallic Nanoparticles for Biomedical Applications

et al. 2007

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In this review, we describe the contribution of peptides to the biomedical applications of metallic nanoparticles. We also discuss strategies for the preparation of peptide-nanoparticle conjugates and the synthesis of the peptides and metallic nanoparticles. An overview of the techniques used for the characterization of the conjugates is also provided. Mainly for biomedical purposes, metallic nanoparticles conjugated to peptides have been prepared from Au and iron oxide (magnetic nanoparticles). Peptides with the capacity to penetrate the plasma membrane are used to deliver nanoparticles to the cell. In addition, peptides that recognize specific cell receptors are used for targeting nanoparticles. The potential application of peptide-nanoparticle conjugates in cancer and Alzheimer's disease therapy is discussed. Several peptide-nanoparticle conjugates show biocompatibility and present a low degree of cytotoxicity. Furthermore, several peptide-metallic nanoparticle conjugates are used for in vitro diagnosis.

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“…In recent years, peptide-coupling reactions have significantly advanced in accord with the development of new peptide-coupling reagents, which has been covered in a number of valuable reviews [1].…”

Section: Introductionmentioning

confidence: 99%