Developments in the Synthesis of Glycopeptides Containing Glycosyl l-Asparagine, l-Serine, and l-Threonine

Garg, Hari G.; Bruch, Karsten von dem; Kunz, Horst

doi:10.1016/s0065-2318(08)60153-5

Cited by 83 publications

(19 citation statements)

References 101 publications

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“…The overall strategy requires an aglycon linker which is a hydroxy acid, that does not lactonize easily, and is preferably UV active. There are few reports on the glycosylation of hydroxy acids (17–19), although precedents on the glycosylation of hydroxy amino acids and, for that matter, the synthesis of glycopeptides are voluminous (20–22). From such studies, it is known that O ‐glycosidic linkages appear to be entirely stable to treatment with concentrated TFA in the absence or presence of carbocation scavengers, particularly while the saccharide retains ester protecting groups (23,24).…”

Section: Resultsmentioning

confidence: 99%

Carbopeptides: carbohydrates as potential templates for de novo design of protein models

Jensen¹,

Bárány²

2000

The Journal of Peptide Research

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De novo design of proteins has evolved into a powerful approach for studying the factors governing protein folding and stability. Among the families of structures frequently studied is the 'four-helix bundle' in which four alpha-helical peptide strands, linked by loops, form a hydrophobic core. Assembly of protein models on a template has been suggested as a way to reduce the entropy of folding. Here we describe the potential use of a carbohydrate as such a template. The monosaccharide D-galactose was per-O-acylated with (Nbeta-Fmoc-betaAla)2O to give a penta-substituted derivative, which was converted to the corresponding glycosyl bromide and used for the glycosylation of 4-hydroxymethylbenzoic acid pentafluorophenyl ester (HMBA-OPfp). The beta-glycosidic carbohydrate template (Nbeta-Fmoc-3Ala)4-beta-D-Galp-(1-O)-MBA-OPfp thus obtained was coupled to a PAL-PEG-PS resin and simultaneously extended at the four arms to yield, after cleavage from the solid support, a carbopeptide with four identical peptide strands. Extension of this concept to, for example, synthesis of novel multiple antigenic peptides (MAPs) and synthesis of carbohydrate clusters can be easily envisioned. The ability to efficiently synthesize such structures sets the stage for further studies to test whether the carbohydrate templates do indeed nucleate folding.

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Section: Resultsmentioning

confidence: 99%

Carbopeptides: carbohydrates as potential templates for de novo design of protein models

Jensen¹,

Bárány²

2000

The Journal of Peptide Research

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“…The chemistry of glycopeptides in general, and of O-glycopeptides especially, has been reviewed [125,126].…”

Section: Lipidated Maps As a Novel Approach In Vaccinementioning

confidence: 99%

Peptide and glycopeptide dendrimers. Part I

Vepřek

Ježek

1999

J. Peptide Sci.

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Recent progress in peptide and glycopeptide chemistry make the preparation of peptide and glycopeptide dendrimers of acceptable purity, with designed structural and immunochemical properties reliable. New methodologies using unprotected peptide building blocks have been developed to further increase possibilities of their design and improve their preparation and separation. Sophisticated design of peptide and glycopeptide dendrimers has led to their use as antigens and immunogens, for serodiagnosis and other biochemical uses including drug delivery. Dendrimers bearing peptide with predetermined secondary structures are useful tools in protein de novo design. This article covers synthesis and applications of multiple antigen peptides (MAPs), multiple antigen glycopeptides (MAGs), multiple antigen peptides based on sequential oligopeptide carriers (MAP-SOCs), glycodendrimers and template-assembled synthetic proteins (TASPs). Part I deals with the development of various structural forms of MAPs as well as their application as antigens, immunogens, and for immunodiagnostic and biochemical purposes. Copyright

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“…The necessary protection and deprotection regimes, the use of solid phase techniques, including the introduction of specific linkers, and coupling methods have all been tailored to be compatible with the presence of carbohydrates. Several excellent reviews 23,[28][29][30][31][32] cover these aspects in detail.…”

Section: Glycopeptide Assemblymentioning

confidence: 99%

Glycoprotein Synthesis: From Glycobiological Tools to Tailor-made Catalysts

Davis

Jones

1999

Synlett

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Abstract:The synthesis of pure, well-defined glycoproteins is essential to the study of the host of biological processes that they mediate. The use of a combined site-directed mutagenesis and chemical modification strategy allows the site-selective synthesis of homogenous glycoproteins, the determination of precise structureactivity relationships and the design of new synthetic catalysts. This general and powerful method is reviewed in the context of existing preparative techniques and the wide-ranging applications of glycoproteins are highlighted

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Developments in the Synthesis of Glycopeptides Containing Glycosyl l-Asparagine, l-Serine, and l-Threonine

Cited by 83 publications

References 101 publications

Carbopeptides: carbohydrates as potential templates for de novo design of protein models

Carbopeptides: carbohydrates as potential templates for de novo design of protein models

Peptide and glycopeptide dendrimers. Part I

Glycoprotein Synthesis: From Glycobiological Tools to Tailor-made Catalysts

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