Efficient synthesis of building blocks for branched rhamnogalacturonan I fragments

Pogosyan, A. V.; Gottwald, A.; Michalik, Dirk; Endreß, Hans-Ulrich; Vogel, Christian

doi:10.1016/j.carres.2013.06.019

Cited by 7 publications

(3 citation statements)

References 28 publications

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“…Among the major monosaccharides identified in watermelon, galactose is a structural component of the backbone in pectin and is a major constituent in arabinogalacto-proteins and RG I and II (Jimenez et al, 2001;Kruger et al, 2008;Pogosyn et al, 2013). High concentrations of galactose are expected in watermelon, as this sugar is present in many pectic polysaccharides.…”

Section: Role Of Neutral Sugar Composition In Watermelon Cell Wall Pomentioning

confidence: 99%

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Cell Wall Polysaccharide Composition of Grafted ‘Liberty’ Watermelon With Reduced Incidence of Hollow Heart Defect

et al. 2021

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Grafting watermelon scions to interspecific squash hybrids has been found to increase fruit firmness. Triploid (seedless) watermelon are prone to hollow heart (HH), an internal fruit disorder characterized by a crack in the placental tissue expanding to a cavity. Although watermelon with lower tissue firmness tend to have a higher HH incidence, associated differences in cell wall polysaccharide composition are unknown. Grafting “Liberty” watermelon to “Carnivor” (interspecific hybrid rootstock, C. moschata × C. maxima) reduced HH 39% and increased tissue firmness by 3 N. Fruit with and without severe HH from both grafted and non-grafted plants were analyzed to determine differences in cell wall polysaccharides associated with grafting and HH. Alcohol insoluble residues (AIR) were sequentially extracted from placental tissue to yield water soluble (WSF), carbonate soluble (CSF), alkali soluble (ASF), or unextractable (UNX) pectic fractions. The CSF was lower in fruit with HH (24.5%) compared to those without HH (27.1%). AIRs were also reduced, hydrolyzed, and acetylated for GC-MS analysis of monosaccharide composition, and a portion of each AIR was methylated prior to hydrolysis and acetylation to produce partially methylated alditol acetates for polysaccharide linkage assembly. No differences in degree of methylation or galacturonic and glucuronic acid concentrations were found. Glucose and galactose were in highest abundance at 75.9 and 82.4 μg⋅mg–1 AIR, respectively, followed by xylose and arabinose (29.3 and 22.0 μg⋅mg–1). Mannose was higher in fruit with HH (p < 0.05) and xylose was highest in fruit from grafted plants (p < 0.05). Mannose is primarily found in heteromannan and rhamnogalacturonan I side chains, while xylose is found in xylogalacturonan or heteroxylan. In watermelon, 34 carbohydrate linkages were identified with galactose, glucose, and arabinose linkages in highest abundance. This represents the most comprehensive polysaccharide linkage analysis to date for watermelon, including the identification of several new linkages. However, total pectin and cell wall composition data could not explain the increased tissue firmness observed in fruit from grafted plants. Nonetheless, grafting onto the interspecific hybrid rootstock decreased the incidence of HH and can be a useful method for growers using HH susceptible cultivars.

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Section: Role Of Neutral Sugar Composition In Watermelon Cell Wall Pomentioning

confidence: 99%

“…Xylose also plays a role in RG II side branches (Brummell, 2006;Karakurt et al, 2008;Kruger et al, 2008). Arabinose is known to be a pectic sugar primarily and is dominant in building type I and II arabinogalactans (AG), which attach to RG I and XG (Pogosyn et al, 2013;Yang et al, 2018).…”

Section: Role Of Neutral Sugar Composition In Watermelon Cell Wall Pomentioning

confidence: 99%

Cell Wall Polysaccharide Composition of Grafted ‘Liberty’ Watermelon With Reduced Incidence of Hollow Heart Defect

et al. 2021

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“…The most frequent form of arabinogalactan side chains is arabinogalactan I, which is a β-(1→4)-galactan with arabinan branches [ 8 , 9 ]. To the best of our knowledge, except for the synthesis of tri- and tetrasaccharide building blocks containing a single galactose unit as a side chain by Vogel and co-workers [ 10 , 11 ], branched RG-I fragments have not previously been addressed by chemical synthesis [ 12 ]. These structures are of great interest because they are useful for the study of pectin and the enzymes involved in both the biosynthesis and degradation of RG-I [ 1 , 2 , 7 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Two Tetrasaccharide Pentenyl Glycosides Related to the Pectic Rhamnogalacturonan I Polysaccharide

et al. 2018

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The synthesis of two protected tetrasaccharide pentenyl glycosides with diarabinan and digalactan branching related to the pectic polysaccharide rhamnogalacturonan I is reported. The strategy relies on the coupling of N-phenyl trifluoroacetimidate disaccharide donors to a common rhamnosyl acceptor. The resulting trisaccharide thioglycosides were finally coupled to an n-pentenyl galactoside acceptor to access the two protected branched tetrasaccharides.

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Protecting Groups at the Anomeric Position of Carbohydrates

Sakonsinsiri

Turnbull

2018

Protecting Groups

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Efficient synthesis of building blocks for branched rhamnogalacturonan I fragments

Cited by 7 publications

References 28 publications

Cell Wall Polysaccharide Composition of Grafted ‘Liberty’ Watermelon With Reduced Incidence of Hollow Heart Defect

Cell Wall Polysaccharide Composition of Grafted ‘Liberty’ Watermelon With Reduced Incidence of Hollow Heart Defect

Synthesis of Two Tetrasaccharide Pentenyl Glycosides Related to the Pectic Rhamnogalacturonan I Polysaccharide

Protecting Groups at the Anomeric Position of Carbohydrates

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