Rhamnogalacturonan II: Chemical Synthesis of a Substructure Including α-2,3-Linked Kdo**

被引：12

作者：

Mancuso, Enzo ^{[1
]}

Romano, Cecilia ^{[1
]}

Trattnig, Nino ^{[2
]}

Gritsch, Philipp ^{[3
]}

Kosma, Paul ^{[2
]}

Clausen, Mads H. ^{[1
]}

机构：

[1] Tech Univ Denmark, Ctr Nanomed & Theranost, Dept Chem, Kemitorvet 207, DK-2800 Lyngby, Denmark

[2] Univ Nat Resources & Life Sci, Dept Chem, 18 Muthgasse, A-1190 Vienna, Austria

[3] TU Wien, Inst Appl Synthet Chem, Getreidemarkt 9, A-1060 Vienna, Austria

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 24期

基金：

奥地利科学基金会;

关键词：

carbohydrates; glycosylation; Kdo; plant cell wall; rhamnogalacturonan;

D O I：

10.1002/chem.202100837

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of a fully deprotected Kdo-containing rhamnogalacturonan II pentasaccharide is described. The strategy relies on the preparation of a suitably protected homogalacturonan tetrasaccharide backbone, through a post-glycosylation oxidation approach, and its stereoselective glycosylation with a Kdo fluoride donor.

引用

页码：7099 / 7102

页数：4

共 34 条

[1] Comparative bioinformatics analysis of the mammalian and bacterial glycomes [J].

Adibekian, Alexander ;

Stallforth, Pierre ;

Hecht, Marie-Lyn ;

Werz, Daniel B. ;

Gagneux, Pascal ;

Seeberger, Peter H. .

CHEMICAL SCIENCE, 2011, 2 (02) :337-344

[2] SYNTHESIS, NMR AND CONFORMATIONAL STUDIES OF SOME 1,4-LINKED DISACCHARIDES [J].

BACKMAN, I ;

JANSSON, PE ;

KENNE, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05) :1383-1388

[3] THE FIRST SYNTHESIS OF 3-DEOXY-D-LYXO-2-HEPTULOSARIC ACID (DHA) DERIVATIVES [J].

BANASZEK, A .

TETRAHEDRON, 1995, 51 (14) :4231-4238

[4] Synthesis of a disaccharide fragment of rhamnogalacturonan II [J].

Buffet, MAJ ;

Rich, JR ;

McGavin, RS ;

Reimer, KB .

CARBOHYDRATE RESEARCH, 2004, 339 (15) :2507-2513

[5] Synthesis of a 2,3,4-triglycosylated rhamnoside fragment of rhamnogalacturonan-II side chain a using a late stage oxidation approach [J].

Chauvin, AL ;

Nepogodiev, SA ;

Field, RA .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :960-966

[6] Synthesis of an apiose-containing disaccharide fragment of rhamnogalacturonan-II and some analogues [J].

Chauvin, AL ;

Nepogodiev, SA ;

Field, RA .

CARBOHYDRATE RESEARCH, 2004, 339 (01) :21-27

[7] SYNTHESIS OF N-ACETYLNEURAMINIC ACID [J].

CORNFORTH, JW ;

FIRTH, ME ;

GOTTSCHALK, A .

BIOCHEMICAL JOURNAL, 1958, 68 :57-&

[8] The gene expression and enzyme activity of plant 3-Deoxy-D-manno-2-octulosonic acid-8-phosphate synthase are preferentially associated with cell division in a cell cycle-dependent manner [J].

Delmas, F ;

Petit, J ;

Joubès, J ;

Séveno, M ;

Paccalet, T ;

Hernould, M ;

Lerouge, P ;

Mouras, A ;

Chevalier, C .

PLANT PHYSIOLOGY, 2003, 133 (01) :348-360

[9] The synthesis of the rhamnogalacturonan II component 3-deoxy-D-manno-2-octulosonic acid (Kdo) is required for pollen tube growth and elongation [J].

Delmas, Frederic ;

Seveno, Martial ;

Northey, Julian G. B. ;

Hernould, Michel ;

Lerouge, Patrice ;

McCourt, Peter ;

Chevalier, Christian .

JOURNAL OF EXPERIMENTAL BOTANY, 2008, 59 (10) :2639-2647

[10] Functional characterisation of a putative rhamnogalacturonan II specific xylosyltransferase [J].

Egelund, Jack ;

Damager, Iben ;

Faber, Kirsten ;

Olsen, Carl-Erik ;

Ulvskov, Peter ;

Petersen, Bent Larsen .

FEBS LETTERS, 2008, 582 (21-22) :3217-3222

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