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Membrane-enclosed multienzyme (MEME) synthesis of 2,7-anhydro-sialic acid derivatives

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논문

Membrane-enclosed multienzyme (MEME) synthesis of 2,7-anhydro-sialic acid derivatives

학술지

Carbohydrate research

저자명

Monestier, Marie; Latousakis, Dimitrios; Bell, Andrew; Tribolo, Sandra; Tailford, Louise E.; Colquhoun, Ian J.; Le Gall, Gwenaelle; Yu, Hai; Chen, Xi; Rejzek, Martin; Dedola, Simone; Field, Robert A.; Juge, Nathalie

초록

<▼1><P>Naturally occurring 2,7-anhydro-alpha-N-acetylneuraminic acid (2,7-anhydro-Neu5Ac) is a transglycosylation product of bacterial intramolecular <I>trans</I>-sialidases (IT-sialidases). A facile one-pot two-enzyme approach has been established for the synthesis of 2,7-anhydro-sialic acid derivatives including those containing different sialic acid forms such as Neu5Ac and N-glycolylneuraminic acid (Neu5Gc). The approach is based on the use of <I>Ruminoccocus gnavus</I> IT-sialidase for the release of 2,7-anhydro-sialic acid from glycoproteins, and the conversion of free sialic acid by a sialic acid aldolase. This synthetic method, which is based on a membrane-enclosed enzymatic synthesis, can be performed on a preparative scale. Using fetuin as a substrate, high-yield and cost-effective production of 2,7-anhydro-Neu5Ac was obtained to high-purity. This method was also applied to the synthesis of 2,7-anhydro-Neu5Gc. The membrane-enclosed multienzyme (MEME) strategy reported here provides an efficient approach to produce a variety of sialic acid derivatives.</P></▼1><▼2><P><B>Highlights</B></P><P>&#x2022;<P>A novel membrane enclosed multiple enzyme approach was developed for the production of 2,7-anhydro-sialic acid derivatives.</P>&#x2022;<P>2,7-anhydro-Neu5Ac was produced in high-yield and high-purity.</P>&#x2022;<P>Neu5Gc-rich glycoprotein was produced using a one-pot two-step enzymatic synthesis.</P>&#x2022;<P>The method allowed the synthesis of a novel compound, 2,7-anhydro-Neu5Gc.</P></P></▼2>

발행연도

2017

발행기관

Elsevier

라이선스

cc-by

ISSN

0008-6215

ISSN

1873-426x

451

페이지

pp.110-117

주제어

Sialic acid enzymatic synthesis; Ruminococcus gnavus; Intramolecular trans-sialidase; 2,7-anhydro-Neu5Ac; 2,7-anhydro-Neu5Gc

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1 2023-12-11

논문; 2017-11-01

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