A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid
The synthesis of monomethyl-esterified trigalacturonans 1-3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycos...
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| Published in | Perkin 1 : an international journal of organic and bio-organic chemistry no. 5; pp. 543 - 551 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Royal Soc Chemistry
01.01.2001
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| Abstract | The synthesis of monomethyl-esterified trigalacturonans 1-3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycosyl donors and acceptors using the n-pentenyl glycosylation technique. Yields of the desired alpha -anomers were in the 50 to 74% range. The trigalactans thus obtained were then subjected to oxidation at C-6. Depending on the protecting group at this position the oxidation either produced the carboxylic acid or the corresponding methyl ester. Hereby, oligomers of galacturonic acid can be prepared with methyl esters introduced in a regiocontrolled fashion. |
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| AbstractList | The synthesis of monomethyl-esterified trigalacturonans 1-3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycosyl donors and acceptors using the n-pentenyl glycosylation technique. Yields of the desired alpha -anomers were in the 50 to 74% range. The trigalactans thus obtained were then subjected to oxidation at C-6. Depending on the protecting group at this position the oxidation either produced the carboxylic acid or the corresponding methyl ester. Hereby, oligomers of galacturonic acid can be prepared with methyl esters introduced in a regiocontrolled fashion. |
| Author | Clausen, MH Jorgensen, MR Madsen, R Thorsen, J |
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| Keywords | ASPERGILLUS-NIGER CELL-WALL GLYCANS ERWINIA-CHRYSANTHEMI-3937 PERFORMANCE PENTENYL GLYCOSIDES CHEMISTRY PHYTOALEXIN ELICITOR ENDOPOLYGALACTURONASE EFFICIENT MASS-SPECTROMETRY |
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| References | NAKAHARA, Y (WOS:A1990EA18100014) 1990; 205 BERTOLINI, M (WOS:A1970I079300010) 1970; 15 Daas, PJH (WOS:000072634000014) 1998; 257 FERRO, V (WOS:A1988P531600020) 1988; 41 SAKAI, T (WOS:A1993BZ68A00006) 1993; 39 Kester, HCM (WOS:000084382700034) 1999; 274 Parenicova, L (WOS:000085379200029) 2000; 345 Roy, C (WOS:000080849100013) 1999; 181 BOCK, K (WOS:A1984TR00200004) 1984; 42 KRAUS, GA (WOS:A1980KR73500004) 1980; 45 Chen, EMW (WOS:A1996UZ79000004) 1996; 29 DESS, DB (WOS:A1991GF10400027) 1991; 113 VISSER J (WOS:000167150100011.27) 1996; 14 Korner, R (WOS:000079593900039) 1999; 71 Shevchik, VE (WOS:000078833200036) 1999; 181 NAKAHARA, Y (WOS:A1989CH65800010) 1989; 194 HASHIMOTO, N (WOS:A1981LT89500043) 1981; 29 FRASERREID, B (WOS:A1992KG62000001) 1992 NAKAHARA, Y (WOS:A1990DG38900027) 1990; 200 Kester, HCM (WOS:000085977300029) 2000; 346 TURVEY, JR (WOS:A19624213B00086) 1962 Magaud, D (WOS:000079989000006) 1998; 314 MANCUSO, AJ (WOS:A1978FC53300041) 1978; 43 UDODONG, UE (WOS:A1992HX16200004) 1992; 48 Magaud, D (WOS:A1997WA54700023) 1997; 38 Benen, JAE (WOS:000078737000004) 1999; 259 Parenicova, L (WOS:000085417700040) 2000; 467 |
| References_xml | – volume: 200 start-page: 363 year: 1990 ident: WOS:A1990DG38900027 article-title: SYNTHETIC STUDIES ON PLANT CELL-WALL GLYCANS .6. SYNTHESIS OF (1-]4)-LINKED GALACTURONIC ACID TRISACCHARIDES, A PROPOSED PLANT WOUND-HORMONE AND A STEREOISOMER publication-title: CARBOHYDRATE RESEARCH contributor: fullname: NAKAHARA, Y – volume: 467 start-page: 333 year: 2000 ident: WOS:000085417700040 article-title: Characterization of a novel endopolygalacturonase from Aspergillus niger with unique kinetic properties publication-title: FEBS LETTERS contributor: fullname: Parenicova, L – volume: 71 start-page: 1421 year: 1999 ident: WOS:000079593900039 article-title: Sequencing of partially methyl-esterified oligogalacturonates by tandem mass spectrometry and its use to determine pectinase specificities publication-title: ANALYTICAL CHEMISTRY contributor: fullname: Korner, R – volume: 194 start-page: 95 year: 1989 ident: WOS:A1989CH65800010 article-title: SYNTHETIC STUDIES ON PLANT-CELL WALL GLYCANS .5. A HIGHLY STEREOCONTROLLED SYNTHESIS OF THE PROPYL GLYCOSIDE OF A DECAGALACTURONIC ACID, A MODEL-COMPOUND FOR THE ENDOGENOUS PHYTOALEXIN ELICITOR-ACTIVE OLIGOGALACTURONIC ACIDS publication-title: CARBOHYDRATE RESEARCH contributor: fullname: NAKAHARA, Y – volume: 314 start-page: 189 year: 1998 ident: WOS:000079989000006 article-title: Synthesis of the two monomethyl esters of the disaccharide 4-O-alpha-D-galacturonosyl-D-galacturonic acid and of precursors for the preparation of higher oligomers methyl uronated in definite sequences publication-title: CARBOHYDRATE RESEARCH contributor: fullname: Magaud, D – volume: 274 start-page: 37053 year: 1999 ident: WOS:000084382700034 article-title: Performance of selected microbial pectinases on synthetic monomethyl-esterified di- and trigalacturonates publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY contributor: fullname: Kester, HCM – volume: 346 start-page: 469 year: 2000 ident: WOS:000085977300029 article-title: Tandem mass spectrometric analysis of Aspergillus niger pectin methylesterase: mode of action on fully methyl-esterified oligogalacturonates publication-title: BIOCHEMICAL JOURNAL contributor: fullname: Kester, HCM – volume: 38 start-page: 241 year: 1997 ident: WOS:A1997WA54700023 article-title: An efficient and highly stereoselective alpha(1->4) glycosylation between two D-galacturonic acid ester derivatives publication-title: TETRAHEDRON LETTERS contributor: fullname: Magaud, D – volume: 42 start-page: 193 year: 1984 ident: WOS:A1984TR00200004 article-title: C-13 NUCLEAR MAGNETIC-RESONANCE DATA FOR OLIGOSACCHARIDES publication-title: ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY contributor: fullname: BOCK, K – volume: 113 start-page: 7277 year: 1991 ident: WOS:A1991GF10400027 article-title: A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: DESS, DB – volume: 15 start-page: 263 year: 1970 ident: WOS:A1970I079300010 article-title: CHLOROACETYL GROUP IN SYNTHETIC CARBOHYDRATE CHEMISTRY publication-title: CARBOHYDRATE RESEARCH contributor: fullname: BERTOLINI, M – volume: 181 start-page: 1652 year: 1999 ident: WOS:000078833200036 article-title: Characterization of the exopolygalacturonate lyase PelX of Erwinia chrysanthemi 3937 publication-title: JOURNAL OF BACTERIOLOGY contributor: fullname: Shevchik, VE – volume: 45 start-page: 4825 year: 1980 ident: WOS:A1980KR73500004 article-title: SYNTHETIC STUDIES TOWARD VERRUCAROL .2. SYNTHESIS OF THE AB RING-SYSTEM publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: KRAUS, GA – volume: 181 start-page: 3705 year: 1999 ident: WOS:000080849100013 article-title: Modes of action of five different endopectate lyases from Erwinia chrysanthemi 3937 publication-title: JOURNAL OF BACTERIOLOGY contributor: fullname: Roy, C – volume: 29 start-page: 1475 year: 1981 ident: WOS:A1981LT89500043 article-title: NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .14. A SIMPLE EFFICIENT PREPARATION OF METHYL-ESTERS WITH TRIMETHYLSILYLDIAZOMETHANE (TMSCHN2) AND ITS APPLICATION TO GAS-CHROMATOGRAPHIC ANALYSIS OF FATTY-ACIDS publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: HASHIMOTO, N – volume: 345 start-page: 637 year: 2000 ident: WOS:000085379200029 article-title: pgaA and pgaB encode two constitutively expressed endopolygalacturonases of Aspergillus niger publication-title: BIOCHEMICAL JOURNAL contributor: fullname: Parenicova, L – start-page: 2119 year: 1962 ident: WOS:A19624213B00086 article-title: SULPHATES OF MONOSACCHARIDES AND DERIVATIVES .4. GALACTOSE 4-SULPHATE publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: TURVEY, JR – start-page: 927 year: 1992 ident: WOS:A1992KG62000001 article-title: N-PENTENYL GLYCOSIDES IN ORGANIC-CHEMISTRY - A CONTEMPORARY EXAMPLE OF SERENDIPITY publication-title: SYNLETT contributor: fullname: FRASERREID, B – volume: 257 start-page: 195 year: 1998 ident: WOS:000072634000014 article-title: Analysis of partially methyl-esterified galacturonic acid oligomers by high-performance anion-exchange chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry publication-title: ANALYTICAL BIOCHEMISTRY contributor: fullname: Daas, PJH – volume: 39 start-page: 213 year: 1993 ident: WOS:A1993BZ68A00006 article-title: PECTIN, PECTINASE, AND PROTOPECTINASE - PRODUCTION, PROPERTIES, AND APPLICATIONS publication-title: ADVANCES IN APPLIED MICROBIOLOGY, VOL 39 contributor: fullname: SAKAI, T – volume: 41 start-page: 813 year: 1988 ident: WOS:A1988P531600020 article-title: AN IMPROVEMENT IN THE PREPARATION OF SOME CARBOHYDRATE BENZYLIDENE ACETALS publication-title: AUSTRALIAN JOURNAL OF CHEMISTRY contributor: fullname: FERRO, V – volume: 205 start-page: 147 year: 1990 ident: WOS:A1990EA18100014 article-title: SYNTHETIC STUDIES ON PLANT-CELL WALL GLYCANS .7. STEREOSELECTIVE TOTAL SYNTHESIS OF DODECAGALACTURONIC ACID, A PHYTOALEXIN ELICITOR OF SOYBEAN publication-title: CARBOHYDRATE RESEARCH contributor: fullname: NAKAHARA, Y – volume: 259 start-page: 577 year: 1999 ident: WOS:000078737000004 article-title: Kinetic characterization of Aspergillus niger N400 endopolygalacturonases I, II and C publication-title: EUROPEAN JOURNAL OF BIOCHEMISTRY contributor: fullname: Benen, JAE – volume: 29 start-page: 129 year: 1996 ident: WOS:A1996UZ79000004 article-title: Nature of sites hydrolyzable by endopolygalacturonase in partially-esterified homogalacturonans publication-title: CARBOHYDRATE POLYMERS contributor: fullname: Chen, EMW – volume: 43 start-page: 2480 year: 1978 ident: WOS:A1978FC53300041 article-title: OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: MANCUSO, AJ – volume: 14 year: 1996 ident: WOS:000167150100011.27 publication-title: PROGR BIOTECHNOLOGY contributor: fullname: VISSER J – volume: 48 start-page: 4713 year: 1992 ident: WOS:A1992HX16200004 article-title: NORMAL-PENTENYL GLYCOSIDES IN THE EFFICIENT ASSEMBLY OF THE BLOOD-GROUP SUBSTANCE-B TETRASACCHARIDE publication-title: TETRAHEDRON contributor: fullname: UDODONG, UE |
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| Title | A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid |
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