S-Fluorenylmethyl protection of the cysteine side chain upon N^α-Fmoc deprotection

• Johannes W. Wehner and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2012, 8, 2149–2155, doi:10.3762/bjoc.8.242

• glycopeptides, for example, in the context of an orthogonal protection/deprotection approach. Experimental General methods Commercially available starting materials and reagents were used without further purification unless otherwise noted. Glycoamino acid derivatives 1 [1], 2 [2], 3 [3], 4 [2], 5 [2] and 6 [3

Antifreeze glycopeptide diastereomers

• Lilly Nagel,
• Carsten Budke,
• Axel Dreyer,
• Thomas Koop and
• Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 1657–1667, doi:10.3762/bjoc.8.190

• Bielefeld, Germany 10.3762/bjoc.8.190 Abstract Antifreeze glycopeptides (AFGPs) are a special class of biological antifreeze agents, which possess the property to inhibit ice growth in the body fluids of arctic and antarctic fish and, thus, enable life under these harsh conditions. AFGPs are composed of 4

• replacement of L-threonine by its allo-L-diastereomer. Both glycopeptides were analyzed regarding their conformational properties, by circular dichroism (CD), and their ability to inhibit ice recrystallization in microphysical experiments. Keywords: bioorganic chemistry; circular dichroism; glycopeptides

• residues [16]. These analogues exhibit a decreased antifreeze activity compared to glycopeptides with the native sequence (Ala-Ala-Thr). Similar results were obtained by Peltier et al. with synthetic AFGP analogues comprising both the N-acetyl galactosamine as the carbohydrate moiety, and alanine by

The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

• Katharina Gallas,
• Gerit Pototschnig,
• Florian Adanitsch,
• Arnold E. Stütz and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2012, 8, 1619–1629, doi:10.3762/bjoc.8.185

• ; carbohydrate elongation; non-natural carbohydrate conjugates; Introduction Glycoconjugates such as glycoproteins, glycopeptides, glycolipids and peptidoglycans are ubiquitous in nature [1]. They are found on cell surfaces and are responsible for processes such as cell–cell interaction, recognition and

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• topologies are computed to match the experimentally determined data [149]. GlyQuest [139] and GlycoMiner [131] are designed for high-throughput analysis of glycopeptides that carry N-glycan chains. Glyco-Peakfinder [133] and GlycoWorkbench [138] cover the complete workflow from recorded experimental data to

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• for the preparation of complex glycopeptides have been drastically improved. The need for homogenous glycopeptides and glycoproteins with defined chemical structures to study diverse biological phenomena further enhances the development of methodologies. Selected recent advances in synthesis and

• applications, in which glycopeptides or glycoproteins serve as tools for biological studies, are reviewed. The importance of specific antibodies directed to the glycan part, as well as the peptide backbone has been realized during the development of synthetic glycopeptide-based anti-tumor vaccines. The fine

• -tuning of native chemical ligation (NCL), expressed protein ligation (EPL), and chemoenzymatic glycosylation techniques have all together enabled the synthesis of functional glycoproteins. The synthesis of structurally defined, complex glycopeptides or glyco-clusters presented on natural peptide

Exceptionally small supramolecular hydrogelators based on aromatic–aromatic interactions

• Junfeng Shi,
• Yuan Gao,
• Zhimou Yang and
• Bing Xu

Beilstein J. Org. Chem. 2011, 7, 167–172, doi:10.3762/bjoc.7.23

• less explored. We have shown that aromatic–aromatic interactions induce the self-assembly of glycopeptides [30] or pentapeptidic derivatives [31] in water to form nanofibers and supramolecular hydrogels. These results, together with the supramolecular hydrogelators made from dipeptide conjugates with

A bivalent glycopeptide to target two putative carbohydrate binding sites on FimH

• Thisbe K. Lindhorst,
• Kathrin Bruegge,
• Andreas Fuchs and
• Oliver Sperling

Beilstein J. Org. Chem. 2010, 6, 801–809, doi:10.3762/bjoc.6.90

• requires further investigation to be conclusive. Keywords: bacterial adhesion; bivalent ligand; ELISA; FimH; glycopeptides; Introduction Bacterial adhesion is a phenomenon which occurs on the surface of host cells as well as on the surface of surgical implants, where it can lead to the formation of

• glycopeptide 16. Boc-deprotection gave the required mannotrioside peptide 17 in the form of its TFA salt. The glycopeptides 8 and 17 were finally ligated via squaric acid employing DES for ligation (Scheme 3). Control of the pH-value during ligation allows sequential substitution [31]: the first amine reacts

Synthesis of glycosylated β³-homo-threonine conjugates for mucin-like glycopeptide antigen analogues

• Florian Karch and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2010, 6, No. 47, doi:10.3762/bjoc.6.47

• Florian Karch Anja Hoffmann-Roder Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, D-55128 Mainz, Germany, Phone: +49-6131-3922417, Fax: +49-6131-3923916 10.3762/bjoc.6.47 Abstract Glycopeptides from the mucin family decorated with tumour-associated

• tumourigenic process and as target structures for cancer immunotherapy [5]. Over the last years, mucin-type glycopeptides decorated with tumour-associated carbohydrate antigens (TACA) have been shown to trigger strong humoral immunity within molecularly defined vaccine prototypes [6][7][8][9][10]. However, the

• development of diverse peptidomimetics for an increasing number of applications [22][23][24][25]. Therefore we contemplated the use of mucin-derived α/β-hybrid glycopeptides as stable mimetics of naturally occurring glycocopeptide antigens for cancer vaccines. We were surprised to see how little precedence

Dimerization of propargyl and homopropargyl 6-azido- 6-deoxy- glycosides upon 1,3-dipolar cycloaddition

• Nikolas Pietrzik,
• Daniel Schmollinger and
• Thomas Ziegler

Beilstein J. Org. Chem. 2008, 4, No. 30, doi:10.3762/bjoc.4.30

• glycosylated building blocks for the combinatorial synthesis of glycopeptides. Synthesis and reaction of compounds 4a and 4a'. Preparation of compounds 4a–g. Dimerization of Glycosides 4a–g under Cu-Catalysis. Supporting Information Supporting Information File 76: Experimental Data Acknowledgements This work