Exploring the Structural Diversity of Mammalian Carbohydrates (“Glycospace”) by Statistical Databank Analysis

Werz, Daniel B.; Ranzinger, René; Herget, Stephan; Adibekian, Alexander; Lieth, Claus‐Wilhelm von der; Seeberger, Peter H.

doi:10.1021/cb700178s

Cited by 259 publications

(230 citation statements)

References 35 publications

(31 reference statements)

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“…A better understanding of the structures of naturally occurring oligosaccharides provides important information on the composition, linkage, branching type of these oligomers [1]. Key building blocks could thus be designed with appropriate protection groups to ensure desired linkage, branch and anomeric selectivity/specificity.…”

Section: Editorialmentioning

confidence: 99%

Towards the Enzymatic Synthesis of Carbohydrates

Cai¹

2012

Organic Chem Current Res

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EditorialThree major repeating biomacromolecules, nucleic acid, protein, and carbohydrate carry out most of the information transfer in living systems. Nucleic acid carries genetic information in the form of DNA and RNA; PCR (Polymerase Chain Reaction), a revolutionary technique developed in 1983 by K. Mullis, has become an indispensable tool in biological and biomedical researches for nucleic acid synthesis. On the other hand, solid-phase peptide synthesis, pioneered by R. B. Merrifield, allows preparation of desired peptides and proteins in vitro in a synthetic manner. However, due to the non-template based biosynthetic pathway of carbohydrates, access structurally defined homogeneous carbohydrate oligomers remains challenging when automated synthesis of oligonucleotides and oligopeptides is common.Inventing new glycosylation reactions has been a long-standing passion for organic and carbohydrate chemists because carbohydrates represent a class of biopolymers which come in a far greater diversity of structures: branching character, stereochemical issue, various types of glycosidic bonds, and posttranslational modifications. A better understanding of the structures of naturally occurring oligosaccharides provides important information on the composition, linkage, branching type of these oligomers [1]. Key building blocks could thus be designed with appropriate protection groups to ensure desired linkage, branch and anomeric selectivity/specificity. With the development of modern organic chemistry, most naturally occurring oligosaccharides and glycoconjugates are synthetically available. However, these chemical approaches are hindered by tedious and time consuming protection and deprotection steps, unsatisfactory stereoselectivities, and low overall yields, making it impractical to prepare long-chain oligosaccharides and polysaccharides.Bioorganic chemistry, the topic of a special issue of Organic Chemistry: Current Research, addresses exactly this difficulty, with reactions catalyzed by carbohydrate processing enzymes found in nature. Dating back half a century, this field was initiated with the growing understanding of sugar biosynthetic pathways [2] and the corresponding key enzymes: glycosyltransferases, glycosidases and their mutants. Though different enzymes utilize distinct donor molecules (e.g. sugar nucleotide, nitrophenyl glycoside, glycosylfluoride) and follow different mechanisms, the concept of "one enzyme-one linkage" makes enzymatic approaches, especially glycosyltransferases, a much more efficient, more regio/stereoselective, and more feasible route to produce oligosaccharides in large scale.With the wide use of glycosyltransferases, attention has shifted to the combination of glycosyltransferase with other enzymes to produce more complex carbohydrates or glycoconjugates with biologically important elements. During the past twenty years, a multi-enzyme one-pot reaction fashion with only one purification step has becoming very popular in carbohydrate synthesis since most of the key enzymes are pro...

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Section: Editorialmentioning

confidence: 99%

Towards the Enzymatic Synthesis of Carbohydrates

Cai¹

2012

Organic Chem Current Res

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“…Statistical analysis of, for example, mammalian oligosaccharides, classified in the GLYCOSCIENCES database, revealed that 36 different building blocks are required to construct about 75% of the 3922 oligosaccharides categorized. [37] However, reduced biostability in vitro and in vivo is a potential problem of many bioorganic macromolecules. On the one hand, degradation can be enhanced due to numerous enzymes.…”

Section: Linear Systemsmentioning

confidence: 99%

Precision Polymers: Monodisperse, Monomer‐Sequence‐Defined Segments to Target Future Demands of Polymers in Medicine

2009

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The established technology platforms of solid‐phase‐supported oligopeptide and oligonucleotide synthesis can be expanded to access fully synthetic macromolecules, preserving both the monodisperse character and the defined monomer sequence. Precision polymers are sequentially assembled from a library of functional building blocks, enabling one to program interaction capabilities or generate functions by sequence‐specific positioning of functionalities. Examples are provided, showing that these monodisperse macromolecules can be conjugated to oligonucleotides, oligopeptides, or poly(ethylene glycol)s. The resulting model systems can contribute to the understanding of complex biomedical‐related processes. Due to the absence of chemical and molecular‐weight distributions in these multifunctional segments, exact correlation of the monomer sequence and (bio)properties is attainable. This is demonstrated by the design of carrier systems that exhibit fine‐tuned interactions with plasmid DNA, actively controlling important steps in DNA delivery and transfection, such as polyplex formation, DNA compression, and release of the cargo.

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“…Glucosamine is the one of the most abundant monosaccharide units with their linkage modes found in mammalian oligosaccharides. [8,9] N-Acetylglucosamine is an abundant hexose that as a monomer or as part of macromolecules plays multiple roles in eukaryotic cells. [10,11] The literature has provided many examples of various glucosamine conjugates [12][13][14][15][16][17][18] which exhibited anticancer, [13,14] neuroprotective, [15] anti-HIV-1, [16] and antimalarial [17] activities.…”

Section: Introductionmentioning

confidence: 99%