A Convenient Microwave-Enhanced Solid-Phase Synthesis of Difficult Peptide Sequences: Case Study of Gramicidin A and CSF114(Glc)

Rizzolo, Fabio; Sabatino, Giuseppina; Chelli, Mario; Rovero, Paolo; Papini, Anna Maria

doi:10.1007/s10989-006-9066-8

Cited by 58 publications

(51 citation statements)

References 13 publications

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“…Peptides with sequences that give rise to beta sheet secondary structures, and those with very hydrophobic regions are most prone to aggregation and are generally the most problematic to synthesize [23,[28][29][30][31][32]. Sequence analysis of UBI29-41, using the Garnier-Robson and Chou-Fasman algorithms, predicted an alpha helical secondary structure for this peptide rather than a beta sheet structure [6,33,34].…”

Section: Discussionmentioning

confidence: 99%

Peptide synthesis, characterization and 68Ga-radiolabeling of NOTA-conjugated ubiquicidin fragments for prospective infection imaging with PET/CT

Ebenhan

Chadwick

Sathekge

et al. 2014

Nuclear Medicine and Biology

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Section: Discussionmentioning

confidence: 99%

Peptide synthesis, characterization and 68Ga-radiolabeling of NOTA-conjugated ubiquicidin fragments for prospective infection imaging with PET/CT

Ebenhan

Chadwick

Sathekge

et al. 2014

Nuclear Medicine and Biology

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“…Recent studies have demonstrated that these improvements are reliable to the MW thermic effects rather than to the specific electromagnetic effect. Lastly, MW-assisted SPPS is compatible with several solid supports, such as polystyrene resins, PEG supports, Wang-resin, chlorotrityl resins, and rink amide resins [78][79][80].…”

Section: Cyclic Peptides and Pseudo-peptides: Mw-irradiation Applied mentioning

confidence: 99%

“…This straightforward synthesis afforded the macrocyclic peptide 202 in high yield (70%) and with high degree of purity. compatible with several solid supports, such as polystyrene resins, PEG supports, Wang-resin, chlorotrityl resins, and rink amide resins [78][79][80]. In this context, MW-assisted SPPS has been applied to the macrocyclization of peptides, pseudopeptides and peptidomimetics (peptoids, β-peptides).…”

Section: Cyclic Peptides and Pseudo-peptides: Mw-irradiation Applied mentioning

confidence: 99%

Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

et al. 2016

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This review describes the recent advances in the microwave-assisted synthesis of 7-membered and larger heterocyclic compounds. Several types of reaction for the cyclization step are discussed: Ring Closing Metathesis (RCM), Heck and Sonogashira reactions, Suzuki-Miyaura cross-coupling, dipolar cycloadditions, multi-component reactions (Ugi, Passerini), etc. Green syntheses and solvent-free procedures have been introduced whenever possible. The syntheses discussed herein have been selected to illustrate the huge potential of microwave in the synthesis of highly functionalized molecules with potential therapeutic applications, in high yields, enhanced reaction rates and increased chemoselectivity, compared to conventional methods. More than 100 references from the recent literature are listed in this review.

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“…The glycopeptide was purified to homogeneity by solid-phase extraction and reverse-phase high-pressure liquid chromatography (HPLC), and further characterized by mass spectrometry and analytical HPLC, as described elsewhere [25]. Letter THIEME…”

Section: Glycopeptide Synthesismentioning

confidence: 99%

Natural Triterpene Glycosides for Antibody Recognition

et al. 2016

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!Multiple sclerosis is an autoimmune disease that affects the central nervous system. The key role of the glycosylation in disease pathogenesis has been previously studied and the synthetic Nglucosylated peptide CSF114(Glc) proved its efficiency in autoantibody recognition in the sera of multiple sclerosis patients. Herein, pure natural triterpene glycosides containing different glycosyl moieties were isolated and tested in multiple sclerosis patientsʼ sera to better understand the role of glycosylation. They were selected taking into account the nature and complexity of their osidic part. Five triterpene glycosides were isolated from several plants with more than 95% purity. The interaction between these glycosides and autoantibodies was evaluated in an enzyme-linked immunosorbent assay measuring IgG and IgM levels in multiple sclerosis patients and healthy blood donors, and the results were compared with those of CSF114(Glc). For each antigen, Mann Whitney and receiver operating characteristic-based analysis were performed to evaluate any statistical significance of the results. The five natural triterpene glycosides showed good capacity to recognize IgMs (sensitivity up to 38 %) with a high specificity (88.9%) for multiple sclerosis patients.Key words multiple sclerosis · triterpene glycosides · autoimmune disease · biomarkers · autoantibody recognition Supporting information available online at http://www.thieme-connect.de/products Complex glycoconjugates, including glycolipids and glycoproteins, are commonly displayed on cell surfaces, where they play crucial roles as intermediaries in extracellular communication and signalling networks [1][2][3]. Therefore, studies on glycan modification patterns of glycoconjugates are a great challenge in medical diagnostic research, offering insight into cellular molecular mechanisms. Moreover, glycoconjugates can be proposed as molecular biomarkers for the disease activity [4,5]. In the field of autoimmunity, different approaches are used to investigate the structures and functions of complex naturally occurring glycoconjugates leading to the identification of autoantigens associated with different autoimmune diseases. In particular, in the context of multiple sclerosis (MS), the development of serum antibodies as biomarkers to be used for the diagnosis, monitoring, and prognosis of such a heterogeneous disease is a challenge because of the ambiguous identification of antigens (Ags) implicated in the disease. MS pathogenesis has not been yet elucidated but includes viral, immunological, and vascular hypotheses [6]. Most of the putative Ags belong to the myelin protein family (i.e., myelin basic protein, proteolipid lipoprotein, and myelin oligodendrocyte glycoprotein). Moreover, pathophysiological post-translational modifications of native Ags can trigger the immune system to generate autoantibodies escaping conventional diagnostic procedures [7]. Thus, autoantibodies against aberrant glycosylations have been hypothesized as diagnostic biomarkers in MS [8,9]. I...

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A Convenient Microwave-Enhanced Solid-Phase Synthesis of Difficult Peptide Sequences: Case Study of Gramicidin A and CSF114(Glc)

Cited by 58 publications

References 13 publications

Peptide synthesis, characterization and 68Ga-radiolabeling of NOTA-conjugated ubiquicidin fragments for prospective infection imaging with PET/CT

Peptide synthesis, characterization and 68Ga-radiolabeling of NOTA-conjugated ubiquicidin fragments for prospective infection imaging with PET/CT

Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

Natural Triterpene Glycosides for Antibody Recognition

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