Structural, Functional, and Mutagenesis Studies of UDP-Glycosyltransferases
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Glycosidic bond
Sweet success: A natural product glycosyltransferase, UrdGT2 from Streptomyces fradiae Tü2717, is the first glycosyltransferase able to catalyze both C-glycosidic and O-glycosidic sugar transfers. These results shed new light on the mechanisms of C-glycosylation of aromatic compounds, which is significant for chemoenzymatic drug lead derivatization as well as for enzymology.
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Streptomyces fradiae
Natural product
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過去10年間は、酵素的な糖転移反応の構造酵素学において大きな進歩が示された時代である。分子生物学の進歩と、高速処理の可能なタンパク質結晶学との組み合わせによって、糖質加水分解酵素の3次元構造があふれるほど明らかにされた。合成化学と構造生物学を共同して適用することによって、多数のオリゴ糖疑似化合物や機械的プローブが作られた。この仕事の多くを支えたのは糖質作用性酵素 (「CAZymes」) の分類であり、今日では非触媒モジュールと合わせて、糖質加水分解酵素、糖質エステラーゼ、多糖リアーゼおよび糖転移酵素を含む範囲にまで拡張されている。それらの構造とグリコシド結合の合成に関わる触媒メカニズムに対するわれわれの理解は、自然のもつ触媒器械および、「グリコシンターゼ」と呼ばれる糖質加水分解酵素変異体によって、最近刺激的に発展した。ここでは「GT-2ファミリー」糖転移酵素である Bocillus subtilis SpsA の構造を含めたそれらの発展を総説し、セルロース、キチン、ビアルロナンおよびNod因子のような生体高分子合成とこの酵素との関連を考察する。
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Glycosyltransferases are key enzymes involved in the biosynthesis of valuable natural products providing an excellent drug-tailoring tool. Herein, we report the identification of two cooperative glycosyltransferases from the sqn gene cluster directing the biosynthesis of saquayamycins in Streptomyces sp. KY40-1: SqnG1 and SqnG2. Gene inactivation of sqnG1 leads to 50-fold decrease in saquayamycin production, while inactivation of sqnG2 leads to complete production loss, suggesting that SqnG2 acts as dual O- and C-glycosyltransferase. Gene inactivation of a third putative glycosyltransferase-encoding gene, sqnG3, does not affect saquayamycin production in a major way, suggesting that SqnG3 has no or a supportive role in glycosylation. The data indicate that SqnG1 and SqnG2 are solely and possibly cooperatively responsible for the sugar diversity observed in saquayamycins 1-7. This is the first evidence of a glycosyltransferase system showing codependence to achieve dual O- and C-glycosyltransferase activity, utilizing NDP-activated d-olivose, l-rhodinose, as well as an unusual amino sugar, presumably 3,6-dideoxy-l-idosamine.
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Keto sugar nucleotides (KSNs) are common and versatile precursors to various deoxy sugar nucleotides, which are substrates for the corresponding glycosyltransferases involved in the biosynthesis of glycoproteins, glycolipids, and natural products. However, there has been no KSN synthesized chemically due to the inherent instability. Herein, the first chemical synthesis of the archetypal KSN TDP-4-keto-6-deoxy-d-glucose (1) is achieved by an efficient and optimized route, providing feasible access to other KSNs and analogues, thereby opening a new avenue for new applications.
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Cyclodextrin glycosyltransferase (CGTase) is a member of the α-amylase family, a large group of enzymes that act on α-glycosidic bonds in starch and related compounds. Over twenty different reaction and product specificities have been found in this family. Although three-dimensional structure elucidation and the biochemical characterization of site-directed mutants have yielded a detailed insight into the mechanism of bond cleavage, the variation in reaction and product specificity is far from understood. This article gives an overview of recent developments in the undersanding and engineering of transglycosylation and hydrolysis specificity in CGTase, which is one of the best-studied α-amylase family enzymes.
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Cleavage (geology)
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Rational design
Natural product
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Nucleic acid structure
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Bacillus anthracis elaborates a secondary cell wall polysaccharide (SCWP) made of 6 to 12 trisaccharide units. Pyruvyl and acetyl substitutions of the distal unit are prerequisites for the noncovalent retention of 22 secreted
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Bacillus anthracis
Carbohydrate conformation
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Introduction Survey of Glycosyltransferases by Type of Sugar Transferred Glycosyltransferases in Oligosaccharide Biosynthesis The Use of Hlycosyltransferases in Analysis of the Structure and Structure-Function Relationships of Oligosaccharides Purification of Glycosyltransferases Concluding Remarks
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Profiling (computer programming)
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