{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T05:39:01Z","timestamp":1790919541388,"version":"4.1.0"},"reference-count":45,"publisher":"Wiley","issue":"36","license":[{"start":{"date-parts":[[2006,11,29]],"date-time":"2006-11-29T00:00:00Z","timestamp":1164758400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2006,12,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The glycoprotein BclA is an important constituent of the exosporium of <jats:italic>Bacillus anthracis<\/jats:italic> spores. This glycoprotein is substituted with an oligosaccharide composed of a \u03b2\u2010<jats:sc>L<\/jats:sc>\u2010rhamnoside substituted with the previously unknown terminal saccharide, 2\u2010<jats:italic>O<\/jats:italic>\u2010methyl\u20104\u2010(3\u2010hydroxy\u20103\u2010methylbutanamido)\u20104,6\u2010dideoxy\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranose, also referred to as anthrose. Anthrose has not been found in spores of <jats:italic>B. cereus<\/jats:italic> and <jats:italic>B. thuringiensis<\/jats:italic>, making it a potential species\u2010specific marker for <jats:italic>B. anthracis.<\/jats:italic> In order to study the antigenicity of anthrose, efficient syntheses of an anthrose\u2010containing trisaccharide and a series of structurally related analogues were developed. The analogues lacked either the methyl ether at C\u20102 or contained modified C\u20104 amino functionalities of anthrose. The synthetic compounds were equipped with an aminopropyl spacer to facilitate conjugation to the carrier proteins mariculture Keyhole Limpet Hemocyanin (mcKLH) and bovine serum albumin (BSA). Serum antibodies of rabbits immunized with live or irradiated spores of <jats:italic>B. anthracis<\/jats:italic> Sterne 34F<jats:sub>2<\/jats:sub> were able to recognize the synthetic trisaccharide\u2013mcKLH conjugate. The specificity of the interaction was confirmed by competitive inhibition with the free\u2010 and BSA\u2010conjugated trisaccharides. Inhibition using the trisaccharide analogues demonstrated that the isovaleric acid moiety of anthrose is an important structural motif for antibody recognition. These data demonstrate that 1) anthrose is a specific antigenic determinant of the <jats:italic>B. anthracis<\/jats:italic> Sterne spore; 2) this antigen is presented to the immune system of rabbits receiving the anthrax live\u2010spore vaccine; 3) synthetic analogues of the oligosaccharide retain the antigenic structure; and 4) the antigenic region is localized to specific terminal groups of the oligosaccharide. Collectively these data provide an important proof\u2010of\u2010concept step in the synthesis and development of spore\u2010specific reagents for detection and targeting of non\u2010protein structures in <jats:italic>B. anthracis<\/jats:italic>.<\/jats:p>","DOI":"10.1002\/chem.200601245","type":"journal-article","created":{"date-parts":[[2006,11,29]],"date-time":"2006-11-29T13:55:30Z","timestamp":1164808530000},"page":"9136-9149","source":"Crossref","is-referenced-by-count":74,"title":["Synthesis and Antigenic Analysis of the BclA Glycoprotein Oligosaccharide from the <i>Bacillus anthracis<\/i> Exosporium"],"prefix":"10.1002","volume":"12","author":[{"given":"Alok S.","family":"Mehta","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elke","family":"Saile","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Zhong","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Therese","family":"Buskas","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Russell","family":"Carlson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elmar","family":"Kannenberg","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yvonne","family":"Reed","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Conrad P.","family":"Quinn","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Geert\u2010Jan","family":"Boons","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,12]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.micro.55.1.647"},{"key":"e_1_2_6_2_2","first-page":"3","volume-title":"Bacillus subtilis and other Gram positive bacteria: biochemistry, physiology, and molecular biology","author":"Priest F. 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