Probing a sialyltransferase’s recognition domain to prepare α(2,8)-linked oligosialosides and analogs

Zhang, Ping; Zuccolo, Amir J.; Li, Wenling; Zheng, Ruixiang Blake; Ling, Chang‐Chun

doi:10.1039/b908933k

Cited by 11 publications

(6 citation statements)

References 26 publications

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“…N ‐Acetylneuraminic acid (sialic acid) has been used for the cellular recognition processes, cell adhesion, and disease states, [72,73] and the sialosides containing a sulfur atom at the anomeric carbon have been investigated as synthetic intermediates [74] . Falconer and coworkers reported one example of the synthesis of unsymmetrical acetyl disulfides sialoside, obtained as a by‐product in the synthesis of the 2‐thioacetyl sialoside ( Scheme 58).…”

Section: Synthesis Of Unsymmetrical Organic Disulfidesmentioning

confidence: 99%

An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides

Ong

Titinchi

Juan

et al. 2021

Helvetica Chimica Acta

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Organic unsymmetrical disulfides have been extensively applied in various academic and industrial fields including intermediates in organic synthesis, agriculture, and food science, natural materials, biochemistry, pharmaceutical and medicine chemistry, polymers, material engineering, etc. They play a crucial role in the fabrication of various biological active sulfur heterocycles. Due to broad and extensive applications, many methods have been developed for the synthesis of unsymmetrical S−S and efforts have been made to improve some issues such as cost, energy efficiency, green chemistry, avoid or minimizing waste generation. Several outstanding review articles have been previously published highlighting the advances of S−S bond formation, in general, using various reagents under different conditions in the absence or presence of oxidants/catalysts. In 2020, a review paper was published by our group focusing on recent developments since 2014 in the synthesis of organic symmetrical disulfides. However, investigations on new catalytic methods are being regularly reported and new types of unsymmetrical disulfides are synthesized. The present overview has attempted to systematically summarize recent advances in the process of unsymmetrical S−S bond formation with a major focus since 2010, highlighting mechanistic considerations, substrate scope, advantages, and limitations. The patents are not studied in this overview.

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Section: Synthesis Of Unsymmetrical Organic Disulfidesmentioning

confidence: 99%

An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides

Ong

Titinchi

Juan

et al. 2021

Helvetica Chimica Acta

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“…In addition, Cst‐II has excellent α2,8‐ST activity using α2,3‐sialosides and α2,6‐sialosides as acceptor substrates 111. The most promising property of Cst‐II is probably its ability to transfer multiple sialic acid moieties onto acceptor sugar molecules (azidoalkyl‐lactoside106,111 or mono‐sialosides112) to achieve the synthesis of ganglioside analogues such as GD3, GT3 or oligosialic acids. Interestingly, Cst‐II also showed the ability to tolerate carbohydrate acceptors with unnatural linkages such as S ‐linked43 GM3 (Figure 8).…”

Section: Bacterial Sialyltransferases and Trans‐sialidasesmentioning

confidence: 99%

Recent Developments in Enzymatic Synthesis of Modified Sialic Acid Derivatives

Withers

2015

Adv Synth Catal

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Sialic acid-containing glycans play important roles in biology, but their synthesisb ys tandard chemical approaches is challenging. Enzymatic assemblyi sg enerally ab etter approach. In the last two decades,anumber of bacterial sialyltransferases (STs) and trans-sialidasesh ave been identifieda nd an umber of them found to exhibit broad substrate specificity.I nt his review,w ew illf ocuso nt he donor and acceptor substrate specificities of these enzymes along with the enzymatic routes employed to prepare sialosidesb earing modificationsa ts pecific positions on the sialic acid carbon skeleton. Understanding the substrate tolerance of these enzymes will help researchers to choose the best biocatalyst for the assemblyo fs pecific sialosides,w hich can be valuable tools in the study of or inhibition of sialidases and STs and sialica cid-binding proteins.I na ddition,t he ability to study these processes using synthetic sialylated glycans will leadt oagreater understanding of their biologya nd willl ead to newt herapeutic targets.1I ntroduction 2S ialic AcidsinN ature 3S ynthesis of Sialic Acid-ContainingO ligosaccharides 4B acterial Sialyltransferases and trans-Sialidases 4

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“…Then, CMP-Neu5Ac is transferred by either of the LOS associated sialyltransferases; CstII (α2,3/8-sialyltransferase) or CstIII (α2,3-sialyltransferase) 11 . Both sialyltransferases belong to the, so far, monospecific CAZy (Carbohydrate-active enzymes database) [12][13][14] glycosyltransferase (GT) family 42 [15][16][17] . Although the presence of GT-42 and N-acetylneuraminate biosynthesis genes (neuABC) is insufficient for expressing molecular mimics, all C. jejuni strains containing this set of genes 8,[18][19][20] (LOS locus classes A, B, C, M, and R) have been shown to synthesize ganglioside-like structures 3,[7][8][9]21 .…”

Section: Introductionmentioning

confidence: 99%

Origin, evolution, and distribution of the molecular machinery for biosynthesis of sialylated lipooligosaccharide structures in Campylobacter coli

Culebro

Machado

Carriço

et al. 2017

Preprint

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Campylobacter jejuni and Campylobacter coli are the most common cause of bacterial gastroenteritis worldwide. Additionally, C. jejuni is the most common bacterial etiological agent in the autoimmune Guillain-Barré syndrome (GBS). Ganglioside mimicry by C. jejuni lipooligosaccharide (LOS) is the triggering factor of the disease. LOS-associated genes involved in the synthesis (neuABC) and transfer of sialic acid (sialyltranferases) are essential in C. jejuni to synthesize ganglioside-like LOS. Therefore these genes have been identified as GBS markers. So far, scarce genetic evidence supports C. coli as a GBS causative agent despite being isolated from GBS patients. Here we show that genes putatively involved in sialic acid transfer are widely distributed in the C. coli population. Evidence found herein suggests that a small group of C. coli strains are very likely to express ganglioside mimics, implying that C. coli can potentially trigger GBS. C. coli also presents a larger repertoire of sialyltransferases than C. jejuni and loss of functions of some those LOS-associated genes has happened during adaptation to agriculture niche. Nevertheless, the activity of these sialyltransferases and their role in shaping C. coli population is yet to be explored.

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Probing a sialyltransferase’s recognition domain to prepare α(2,8)-linked oligosialosides and analogs

Abstract: We report the first observation that a monosialyl residue is the essential structural element recognized by the enzyme CST-II; this has resulted in an attractive route to synthesize a series of alpha(2,8)-linked oligosialic acids and their thioanalogs in one step.

Cited by 11 publications

References 26 publications

An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides

An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides

Recent Developments in Enzymatic Synthesis of Modified Sialic Acid Derivatives

Origin, evolution, and distribution of the molecular machinery for biosynthesis of sialylated lipooligosaccharide structures in Campylobacter coli

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