8-1,2-Oligomannan phosphorylase-mediated synthesis of potential oligosaccharide vaccine candidates
8-(1,2)-Mannan antigens incorporated into vaccines candidates for immunization studies, showed that antibodies raised against 8-(1,2)-mannotriose antigens can protect against disseminated candidiasis. Until recently, 8-(1,2)-mannans could only be obtained by isolation from microbial cultures, or by...
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| Published in | Carbohydrate research Vol. 528 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier
01.06.2023
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| Abstract | 8-(1,2)-Mannan antigens incorporated into vaccines candidates for immunization studies, showed that antibodies raised against 8-(1,2)-mannotriose antigens can protect against disseminated candidiasis. Until recently, 8-(1,2)-mannans could only be obtained by isolation from microbial cultures, or by lengthy synthetic strategies involving protecting group manipulation. The discovery of two 8-(1,2)-mannoside phos-phorylases, Teth514_1788 and Teth514_1789, allowed efficient access to these compounds. In this work, Teth514_1788 was utilised to generate 8-(1,2)-mannan antigens, tri-and tetra-saccharides, decorated with a conjugation tether at the reducing end, suitable to be incorporated on a carrier en-route to novel vaccine can-didates, illustrated here by conjugation of the trisaccharide to BSA. |
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| AbstractList | 8-(1,2)-Mannan antigens incorporated into vaccines candidates for immunization studies, showed that antibodies raised against 8-(1,2)-mannotriose antigens can protect against disseminated candidiasis. Until recently, 8-(1,2)-mannans could only be obtained by isolation from microbial cultures, or by lengthy synthetic strategies involving protecting group manipulation. The discovery of two 8-(1,2)-mannoside phos-phorylases, Teth514_1788 and Teth514_1789, allowed efficient access to these compounds. In this work, Teth514_1788 was utilised to generate 8-(1,2)-mannan antigens, tri-and tetra-saccharides, decorated with a conjugation tether at the reducing end, suitable to be incorporated on a carrier en-route to novel vaccine can-didates, illustrated here by conjugation of the trisaccharide to BSA. |
| ArticleNumber | 108807 |
| Author | Kohler, Dominic Winsbury, Rebecca Voglmeir, Josef Field, Robert A. Nepogodiev, Sergey A. Pergolizzi, Giulia Wang, Meng Ahmadipour, Sanaz Chessa, Simona Dedola, Simone |
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| Keywords | 8--Oligomannan phosphorylase Glycoconjugate vaccines Candida pathogen Click chemistry 8--Mannan antigen |
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| References | Drula, E (WOS:000743496700069) 2022; 50 Pergolizzi, G (WOS:000413686800004) 2017; 24 Kim, Kweon (BCI:BCI199396071844) 1993; 16 O'Neill, EC (WOS:000349085900006) 2015; 403 Liu, J (WOS:000626844200027) 2021; 11 Rollenske, T (WOS:000433041500027) 2018; 19 Krasnova, L (WOS:000460996500001) 2019; 141 Tanaka, T (WOS:000266674700015) 2009 HAN, YM (WOS:A1995RE84200045) 1995; 63 Polakova, M (WOS:000263648200012) 2009; 2009 Cuadros, J (WOS:000264897200011) 2009; 333 O'Neill, EC (WOS:000413320300012) 2017; 451 LEMIEUX, RU (WOS:A1975AH59900035) 1975; 97 Dai, LH (WOS:000702881400008) 2021; 579 Ahmadipour, S (WOS:000473116000005) 2019; 21 Singh, RP (WOS:000504784100001) 2020; 21 Chiku, K (WOS:000346375400058) 2014; 9 Hopkins, R. (000987008300001.18) 2014; 53706 Yin, M (WOS:000457801200001) 2019; 10 FAILLE, C (WOS:A1992KF75500004) 1992; 236 |
| References_xml | – volume: 451 start-page: 118 year: 2017 ident: WOS:000413320300012 article-title: Cellodextrin phosphorylase from Ruminiclostridium thermocellum: X-ray crystal structure and substrate specificity analysis publication-title: CARBOHYDRATE RESEARCH doi: 10.1016/j.carres.2017.07.005 contributor: fullname: O'Neill, EC – volume: 9 start-page: ARTN e114882 year: 2014 ident: WOS:000346375400058 article-title: Discovery of Two beta-1,2-Mannoside Phosphorylases Showing Different Chain-Length Specificities from Thermoanaerobacter sp X-514 publication-title: PLOS ONE doi: 10.1371/journal.pone.0114882 contributor: fullname: Chiku, K – volume: 333 start-page: 78 year: 2009 ident: WOS:000264897200011 article-title: Reactions of lysine with montmorillonite at 80 degrees C: Implications for optical activity, H+ transfer and lysine-montmorillonite binding publication-title: JOURNAL OF COLLOID AND INTERFACE SCIENCE doi: 10.1016/j.jcis.2009.01.031 contributor: fullname: Cuadros, J – volume: 97 start-page: 4076 year: 1975 ident: WOS:A1975AH59900035 article-title: PROPERTIES OF A SYNTHETIC ANTIGEN RELATED TO HUMAN BLOOD-GROUP LEWIS-A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LEMIEUX, RU – volume: 16 start-page: 94 year: 1993 ident: BCI:BCI199396071844 article-title: Preparation of azides from hydrazines by using dinitrogen tetroxide as nitrosonium ion source publication-title: Archives of Pharmacal Research (Seoul) contributor: fullname: Kim, Kweon – volume: 236 start-page: 17 year: 1992 ident: WOS:A1992KF75500004 article-title: COMPLETE H-1-RESONANCE AND C-13-RESONANCE ASSIGNMENTS FOR D-MANNOOLIGOSACCHARIDES OF THE BETA-D-(1-]2)-LINKED SERIES RELEASED FROM THE PHOSPHOPEPTIDOMANNAN OF CANDIDA-ALBICANS VW-32 (SEROTYPE-A) publication-title: CARBOHYDRATE RESEARCH contributor: fullname: FAILLE, C – volume: 11 start-page: 2763 year: 2021 ident: WOS:000626844200027 article-title: Facile Enzymatic Synthesis of Diverse Naturally-Occurring beta-D-Mannopyranosides Catalyzed by Glycoside Phosphorylases publication-title: ACS CATALYSIS doi: 10.1021/acscatal.0c05378 contributor: fullname: Liu, J – volume: 21 start-page: 1043 year: 2020 ident: WOS:000504784100001 article-title: Preparative and Kinetic Analysis of beta-1,4-and beta-1,3-Glucan Phosphorylases Informs Access to Human Milk Oligosaccharide Fragments and Analogues Thereof publication-title: CHEMBIOCHEM doi: 10.1002/cbic.201900440 contributor: fullname: Singh, RP – volume: 579 start-page: 54 year: 2021 ident: WOS:000702881400008 article-title: Structural investigation of a thermostable 1,2-0-mannobiose phosphorylase from Thermoanaerobacter sp. X-514 publication-title: BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS doi: 10.1016/j.bbrc.2021.09.046 contributor: fullname: Dai, LH – volume: 24 start-page: 696 year: 2017 ident: WOS:000413686800004 article-title: Glycan Phosphorylases in Multi-Enzyme Synthetic Processes publication-title: PROTEIN AND PEPTIDE LETTERS doi: 10.2174/0929866524666170811125109 contributor: fullname: Pergolizzi, G – volume: 21 start-page: 4415 year: 2019 ident: WOS:000473116000005 article-title: Chemoenzymatic Synthesis of C6-Modified Sugar Nucleotides To Probe the GDP-D-Mannose Dehydrogenase from Pseudomonas aeruginosa publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.9b00967 contributor: fullname: Ahmadipour, S – volume: 403 start-page: 23 year: 2015 ident: WOS:000349085900006 article-title: Enzymatic synthesis using glycoside phosphorylases publication-title: CARBOHYDRATE RESEARCH doi: 10.1016/j.carres.2014.06.010 contributor: fullname: O'Neill, EC – volume: 10 start-page: ARTN 145 year: 2019 ident: WOS:000457801200001 article-title: Advances in Research on Immunoregulation of Macrophages by Plant Polysaccharides publication-title: FRONTIERS IN IMMUNOLOGY doi: 10.3389/fimmu.2019.00145 contributor: fullname: Yin, M – volume: 19 start-page: 617 year: 2018 ident: WOS:000433041500027 article-title: Cross-specificity of protective human antibodies against Klebsiella pneumoniae LPS O-antigen publication-title: NATURE IMMUNOLOGY doi: 10.1038/s41590-018-0106-2 contributor: fullname: Rollenske, T – volume: 141 start-page: 3735 year: 2019 ident: WOS:000460996500001 article-title: Oligosaccharide Synthesis and Translational Innovation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.8b11005 contributor: fullname: Krasnova, L – volume: 2009 start-page: 870 year: 2009 ident: WOS:000263648200012 article-title: Synthesis of beta-(1 -> 2)-Linked Oligomannosides publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200801024 contributor: fullname: Polakova, M – volume: 63 start-page: 2714 year: 1995 ident: WOS:A1995RE84200045 article-title: ANTIBODY-RESPONSE THAT PROTECTS AGAINST DISSEMINATED CANDIDIASIS publication-title: INFECTION AND IMMUNITY contributor: fullname: HAN, YM – volume: 53706 start-page: 17 year: 2014 ident: 000987008300001.18 publication-title: Division of University Housing contributor: fullname: Hopkins, R. – volume: 50 start-page: D571 year: 2022 ident: WOS:000743496700069 article-title: The carbohydrate-active enzyme database: functions and literature publication-title: NUCLEIC ACIDS RESEARCH doi: 10.1093/nar/gkab1045 contributor: fullname: Drula, E – start-page: 3378 year: 2009 ident: WOS:000266674700015 article-title: One-step conversion of unprotected sugars to beta-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b905761g contributor: fullname: Tanaka, T |
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| Title | 8-1,2-Oligomannan phosphorylase-mediated synthesis of potential oligosaccharide vaccine candidates |
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