Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus

Ma, Zuchao; Zhang, Jianjun; Kong, Fanzuo

doi:10.1016/j.carres.2003.09.030

Cited by 10 publications

(2 citation statements)

References 16 publications

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“…BSmB [16], GlcNAc-Mal [17], GlcNAc-OBn (O-benzyl-N-acetylglucosamine) [18] and GlcNAc-OMe (O-methyl-Nacetylglucosamine) [19] were chemically synthesized as described previously. BS-Fos (bacillithiol-fosfomycin) was enzymatically synthesized via FosB-catalysed S-conjugation of BSH with fosfomycin [16].…”

Section: Methodsmentioning

confidence: 99%

Cross-functionalities ofBacillusdeacetylases involved in bacillithiol biosynthesis and bacillithiol-S-conjugate detoxification pathways

Fang

Roberts

Weidman

et al. 2013

Biochemical Journal

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BshB, a key enzyme in bacillithiol biosynthesis, hydrolyses the acetyl group from N-acetylglucosamine malate to generate glucosamine malate. In Bacillus anthracis, BA1557 has been identified as the N-acetylglucosamine malate deacetylase (BshB); however, a high content of bacillithiol (~70%) was still observed in the B. anthracis ∆BA1557 strain. Genomic analysis led to the proposal that another deacetylase could exhibit cross-functionality in bacillithiol biosynthesis. In the present study, BA1557, its paralogue BA3888 and orthologous Bacillus cereus enzymes BC1534 and BC3461 have been characterized for their deacetylase activity towards N-acetylglucosamine malate, thus providing biochemical evidence for this proposal. In addition, the involvement of deacetylase enzymes is also expected in bacillithiol-detoxifying pathways through formation of S-mercapturic adducts. The kinetic analysis of bacillithiol-S-bimane conjugate favours the involvement of BA3888 as the B. anthracis bacillithiol-S-conjugate amidase (Bca). The high degree of specificity of this group of enzymes for its physiological substrate, along with their similar pH-activity profile and Zn²⁺-dependent catalytic acid-base reaction provides further evidence for their cross-functionalities.

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Section: Methodsmentioning

confidence: 99%

Cross-functionalities ofBacillusdeacetylases involved in bacillithiol biosynthesis and bacillithiol-S-conjugate detoxification pathways

Fang

Roberts

Weidman

et al. 2013

Biochemical Journal

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show abstract

“…The methyl-and benzyl-glycosides of glucosamine (10 17 and 11) were prepared by hydrazinolysis of their N-acetyl precursors 8 18 and 9 19 at 120 • C (Scheme 1a). The strategy for the solid phase reactions was to immobilise the cysteine motif onto a polystyrene resin via an S-trityl linkage as this would also serve to protect the thiol during the amide coupling reaction.…”

Section: Resultsmentioning

confidence: 99%

Mycothiol disulfide reductase: solid phase synthesis and evaluation of alternative substrate analogues

et al. 2008

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Glycoside Synthesis from 1‐Oxygen Substituted Glycosyl Donors: Sections 3.1 and 3.2

Ryan

Gin

Zhu

et al. 2008

Handbook of Chemical Glycosylation

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Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus

Cited by 10 publications

References 16 publications

Cross-functionalities ofBacillusdeacetylases involved in bacillithiol biosynthesis and bacillithiol-S-conjugate detoxification pathways

Cross-functionalities ofBacillusdeacetylases involved in bacillithiol biosynthesis and bacillithiol-S-conjugate detoxification pathways

Mycothiol disulfide reductase: solid phase synthesis and evaluation of alternative substrate analogues

Glycoside Synthesis from 1‐Oxygen Substituted Glycosyl Donors: Sections 3.1 and 3.2

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