De Novo Synthesis of Uronic Acid Building Blocks for Assembly of Heparin Oligosaccharides

Adibekian, Alexander; Bindschädler, Pascal; Timmer, Mattie S. M.; Noti, Christian; Schützenmeister, Nina; Seeberger, Peter H.

doi:10.1002/chem.200700141

Cited by 63 publications

(38 citation statements)

References 80 publications

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“…ΔHexA(2S)-GlcN(NS,6S)-GlcAGlcN(NS,6S) ) Uronic acid building blocks for heparin oligosaccharides MALDI Synthesis by stereoselective elongation of thio-acetal protected dialdehydes (Adibekian, et al, 2007) N-linked glycans 13 C-Neu5Ac-labelled biantennary glycans MALDI Synthesised with [1,2,3,10,11-13 C]-CMP-β-Neu5Ac (Macnaughtan, et al, 2008) HexNAc-(Pent)HexA-(Pent)Hex-Hex-HexNAc-Asn…”

Section: Maldi (Dhb)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Section: Maldi (Dhb)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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“…Structural representation of (A and B) dialdehydes 1 and 2 (compounds 12a and 17 of reference ) utilized, respectively, for synthesis of (C) d ‐GlcA and (D) l ‐IdoA building blocks (compounds 16 and 22 of reference ). The abbreviation of protecting groups are as follows: Bn = benzil, Lev = levulinoyl, Me = methyl, Piv = pivaloyl, SEt = silyl ether.…”

Section: Synthetic Gagsmentioning

confidence: 99%

A Dilemma in the Glycosaminoglycan‐Based Therapy: Synthetic or Naturally Unique Molecules?

Pomin

2015

Medicinal Research Reviews

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Glycosaminoglycans (GAGs) are widely explored in the biomedical market as functional ingredients in pharmaceutical or nutraceutical preparations. This extensive application of GAGs is justified by their multiple activities across several systems including, but not limited to, coagulation, thrombosis, inflammation, cancer, angiogenesis, cell differentiation, tissue repair, and microbial infections. Therapeutic GAGs are commonly extracted from mammalian tissues. Although functional in diverse systems, mammalian GAGs present serious downsides in therapy such as contamination risk from the mammalian tissues. In order to overcome some of the downsides, two new GAG sources have been appearing as alternatives to the mammalian-derived molecules. They are the synthetic GAGs and those extracted from nonmammalian origins such as invertebrate animals. This report overviews the general aspects of each GAG alternative and compares critically their pros and cons attributes in light of the prospects for the future of GAG-based therapy.

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“…Particularly advantageous is the preparation of carbohydrate building blocks that can directly be used in the synthesis of oligosaccharides or other glycoconjugates without further protecting group transformations. [6] In this context, we recently described de novo approaches towards different classes of amino sugars and their mimetics starting from enantiopure 1,2-oxazines, [7] which are surprisingly versatile intermediates for the stereoselective synthesis of a variety of carbohydrate related compounds such as polyhydroxylated pyrrolidines, azetidines or polyols. [8] Among these differently configured C2-branched 4-amino sugars A have been generated from bicyclic compounds B by a sequence of glycosidation reaction, stereoselective carbonyl reduction and reductive cleavage of the N À O bond (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Internally Protected Amino Sugar Equivalents from Enantiopure 1,2‐Oxazines: Synthesis of Variably Configured Carbohydrates with C‐Branched Amino Sugar Units

Pfrengle

Reißig

2010

Chemistry A European J

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A stereodivergent synthesis of differently configured C2-branched 4-amino sugar derivatives was accomplished. The Lewis acid mediated rearrangement of phenylthio-substituted 1,2-oxazines delivered glycosyl donor equivalents that can directly be employed in glycosidation reactions. Treatment with methanol provided internally protected amino sugar equivalents that have been transformed into the stereoisomeric methyl glycosides 28, ent-28, 29, ent-29 and 34 in two simple reductive steps. Reaction with natural carbohydrates or bicyclic amino sugar precursors allowed the synthesis of homo-oligomeric di- and trisaccharides 44, 46 and 47 or a hybrid trisaccharide 51 with natural carbohydrates. Access to a bivalent amino sugar derivative 54 was accomplished by reaction of rearrangement product 10 with 1,5-pentanediol. Alternatively, when a protected L-serine derivative was employed as glycosyl acceptor, the glycosylated amino acid 60 was efficiently prepared in few steps. In this report we describe the synthesis of unusual amino sugar building blocks from enantiopure 1,2-oxazines that can be attached to natural carbohydrates or natural product aglycons to produce new natural product analogues with potential applications in medicinal chemistry.

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De Novo Synthesis of Uronic Acid Building Blocks for Assembly of Heparin Oligosaccharides

Cited by 63 publications

References 80 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

A Dilemma in the Glycosaminoglycan‐Based Therapy: Synthetic or Naturally Unique Molecules?

Internally Protected Amino Sugar Equivalents from Enantiopure 1,2‐Oxazines: Synthesis of Variably Configured Carbohydrates with C‐Branched Amino Sugar Units

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