Found 2 structures.
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1. Compound ID: 13715
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R-3HOBut-(1-7)-b-Psep5Ac-(2-6)-a-D-Glcp-(1-6)-+
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-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_147450,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_21,SB_23,SB_24,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 5458
Kenyon JJ, Arbatsky NP, Shashkov AS, Shneider MM, Popova AV, Hall RM, Knirel YA "Production of the K16 capsular polysaccharide by Acinetobacter baumannii ST25 isolate D4 involves a novel glycosyltransferase encoded in the KL16 gene cluster" -
International Journal of Biological Macromolecules 128 (2019) 101-106
A new capsular polysaccharide (CPS) biosynthesis gene cluster, KL16, was found in the genome sequence of a clinical Acinetobacter baumannii ST25 isolate, D4. The variable part of KL16 contains a module of genes for synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic acid (5,7-di-N-acetylpseudaminic acid, Pse5Ac7Ac), a gene encoding ItrA3 that initiates the CPS synthesis with d-GlcpNAc, and two glycosyltransferase (Gtr) genes. The K16 CPS was studied by sugar analysis and Smith degradation along with 1D and 2D 1H and 13C NMR spectroscopy, and shown to be built up of linear trisaccharide repeats containing d-galactose (d-Gal), N-acetyl-d-glucosamine (d-GlcNAc), and Pse5Ac7Ac. The d-Galp residue is linked to the d-GlcpNAc initiating sugar via a β-(1→3) linkage evidently formed by a Gtr5 variant, Gtr5K16, encoded in KL16. This reveals an altered or relaxed substrate specificity of this variant as the majority of Gtr5-type glycosyltransferases have previously been shown to form a β-d-Galp-(1→3)-d-GalpNAc linkage. The β-Psep5Ac7Ac-(2→4)-d-Galp linkage is predicted to be formed by the other glycosyltransferase, Gtr37, which does not match members of any known glycosyltransferase family.
Acinetobacter baumannii, capsular polysaccharide, 5, glycosyltransferase, 7-Di-N-acetylpseudaminic acid, KL16 K locus
NCBI PubMed ID: 30664967Publication DOI: 10.1016/j.ijbiomac.2019.01.080Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: J.J. Kenyon
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Antimicrobial Chemotherapy, Smolensk State Medical University, Smolensk, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, Smith degradation, function analysis of gene clusters
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2. Compound ID: 16257
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R-3HOBut-(1-7)-b-Psep5Ac-(2-6)-a-D-Galp-(1-6)-+
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-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
; -3)[Ac(1-2)]bDGalpN(1-3)[Ac(1-5)[Ac(1-7)]bXPsep(2-6)bDGlcp(1-6)]bDGalp(1-
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_134624,IEDB_134627,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_147450,IEDB_151528,IEDB_190606,IEDB_742248,SB_163,SB_165,SB_166,SB_187,SB_195,SB_21,SB_23,SB_24,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 6301
Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" -
Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.
chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal
NCBI PubMed ID: 35750381Publication DOI: 10.1016/S1875-5364(22)60177-8Journal NLM ID: 101504416Publisher: Beijing: Science Press; Elsevier
Correspondence: J. Yin
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
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