Synthesis of 1-Glyceritol D-Galactopyranosides.

Wickberg, Börje; Jensen, R. B.; Vardheim, S. V.; Linderot, T.; Veige, S.; Diczfalusy, E.

doi:10.3891/acta.chem.scand.12-1187

Cited by 91 publications

(18 citation statements)

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“…Porphyra is one of the most extensively eaten macroalgae in southeast Asia because of its high nutritional value (Abbott, 1988). Whereas the heteroside floridoside (α-D-galactopyranosyl-(1-2)-glycerol) is considered to be the main photosynthetic and reserve product in all orders of the Rhodophyta except the Ceramiales, members of the Bangiales such as Porphyra and Bangia also contain two isomeric forms of floridoside, D-isofloridoside (α-D-galactopyranosyl-(1-1)-D-glycerol) and L-isofloridoside (α-D-galactopyranosyl-(1-1)-L-glycerol) (Wickberg, 1958 ;Meng et al, 1987 ;Karsten et al, 1993). The total of all heterosides in both genera can account for more than 30% of the dry weight (Karsten et al, 1993).…”

Section: mentioning

confidence: 99%

Seasonal variation in heteroside concentrations of field‐collected Porphyra species (Rhodophyta) from different biogeographic regions

Karsten

1999

New Phytologist

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Eight different species of the red algal genus Porphyra from different biogeographic regions in Europe, Africa, North America, Asia and Australia were collected over the course of the respective growth season and surveyed for the qualitative and quantitative occurrence of the low molecular weight carbohydrates, floridoside, Disofloridoside and L-isofloridoside. Except for Porphyra saldanhae from South Africa, all species tested exhibited clear seasonal variations in their heteroside composition. Whereas Porphyra dioica and Porphyra umbilicalis from the North Sea showed highest carbohydrate concentrations in spring and summer, those of Porphyra leucosticta from Spain were highest in winter. The red algae studied exhibited highest concentrations of heteroside at different seasons, some in winter, others in spring or summer. The composition of the three compounds varied among the species studied. In P. columbina from Australia, L-isofloridoside was always quantitatively dominant, while floridoside was the major component in P. dioica. Usually D-isofloridoside was present in small concentrations, except in P. perforata from the Pacific coast of the USA where it occurred in equal concentrations with floridoside and L-isofloridoside. The results point to species-specific different enzymic activities of the underlying anabolic pathways. Correlations between the heteroside concentrations and various prevailing environmental parameters are detectable but do not reveal a general response of Porphyra. Data from the literature prove that numerous physical factors determine the growth patterns of various Porphyra species in different biogeographic regions. Of these, photoperiod, temperature and nutrients are the most important. Highest heteroside concentrations in the Porphyra species studied always coincided with enhanced growth, and this relationship determined that growth, though related to abiotic conditions, was also promoted by maximum carbohydrate content. The multiple physiological function of floridoside, D-isofloridoside and L-isofloridoside as osmolytes, compatible solutes and carbon reserves is discussed in relation to the environmental stresses that Porphyra species usually experience in their upper intertidal habitats.

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Section: mentioning

confidence: 99%

Seasonal variation in heteroside concentrations of field‐collected Porphyra species (Rhodophyta) from different biogeographic regions

Karsten

1999

New Phytologist

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“…[20] Then O-allylation de-O-isopropylidenation [21] and regioselective introduction of the TBDPS group gave intermediate 8 (Scheme 3) which was used for the attachment of the MPM group. [20] Then O-allylation de-O-isopropylidenation [21] and regioselective introduction of the TBDPS group gave intermediate 8 (Scheme 3) which was used for the attachment of the MPM group.…”

Section: Methodsmentioning

confidence: 99%

“…The required building block 4 was obtained from commercially available 1,2-O-isopropylidene-sn-glycerol. [20] Then O-allylation de-O-isopropylidenation [21] and regioselective introduction of the TBDPS group gave intermediate 8 (Scheme 3) which was used for the attachment of the MPM group. De-O-allylation of this MPM-protected intermediate, and then reaction with benzyloxybis(diisopropylamino)phosphane [22] in the presence of tetrazole afforded building block 5 (Scheme 2).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of the First Fully Active Lipoteichoic Acid.

et al. 2003

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“…As a consequence, the palmitoyl should be connected with 2-OH. Finally, the absolute stereochemistry of C-2 in the glycerol portion of compound 1 was tentatively assigned as R, the same as that of model compound 3 by either comparing the specific rotation of 2 with that reported previously [8] or comparing the optical rotation of 1 with that of 3 {[a] D þ 43.0 (c 1, MeOH)} [6] according to Hyraeb's rule [9]. On the basis of these findings, the structure of the new glycolipid 1 was determined as…”

Section: Introductionmentioning

confidence: 99%