Branched-Chain Sugars

Beck, Erwin

doi:10.1007/978-3-642-68275-9_4

Cited by 6 publications

(6 citation statements)

References 132 publications

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“…Consistent with this suggestion is the increased incorporation of newly assimilated radiolabel into CA1P when assimilation takes place at low irradiance (13); conditions under which FBP concentrations would be relatively high (15). In leaves of an alpine primrose (Primula clusiana Tausch), HBP is metabolized to hamamelose 2 1 -phosphate, hamamelose 5-phosphate and hamamelose (14,16). Hamamelose (2-hydroxymethyl-D-ribose) is very widely distributed among plant species (17).…”

mentioning

confidence: 82%

Conversion of D-Hamamelose into 2-Carboxy-D-arabinitol and 2-Carboxy-D-arabinitol 1-Phosphate in Leaves of Phaseolus vulgaris L.

Andralojc¹,

Keys²,

Martindale³

et al. 1996

Journal of Biological Chemistry

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[1-14C]Hamamelose (2-hydroxymethyl-D-ribose) was synthesized by reaction of ribulose 5-phosphate with potassium [14C]cyanide, catalytic hydrogenation of the resulting cyanohydrin, and dephosphorylation of the product. Its identity was established by a chromatographic comparison with hamamelose isolated from the bark of witch hazel (Hamamelis virginiana L.). Following vacuum infiltration of the [1-14C]hamamelose into leaf discs from Phaseolus vulgaris L., 14C-labeled 2carboxy-D-arabinitol (CA) and 2-carboxy-D-arabinitol 1-phosphate (CA1P) were formed, in the dark. Conversion of hamamelose to both CA and CA1P in the leaf discs was inhibited by dithiothreitol and sodium fluoride, although at high concentrations of these inhibitors conversion into CA was still evident when conversion into CA1P was totally inhibited. Wheat (Triticum aestivum L.) leaves converted hamamelose into CA without formation of CA1P. Leaves from P. vulgaris contained 68 nmol.g-1 fresh weight of hamamelose in the light and 35 nmol.g-1 fresh weight in the dark. A pathway for the biosynthesis of CA1P from Calvin cycle intermediates is proposed which includes the sequence: hamamelose --> CA --> CA1P.

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confidence: 82%

Conversion of D-Hamamelose into 2-Carboxy-D-arabinitol and 2-Carboxy-D-arabinitol 1-Phosphate in Leaves of Phaseolus vulgaris L.

Andralojc¹,

Keys²,

Martindale³

et al. 1996

Journal of Biological Chemistry

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“…Admittedly, the correct term is more circumstantial than 2CA1P, but since this compound is a member of a naturally occurring family of branched-chain monosaccharides, a simple common name, viz. HA2'P, should be used (for a review of those compounds, see Beck [1]). …”

Section: Proof Of Identity Of 2-carboxyarabinitol and D-hamamelonic Acidmentioning

confidence: 99%

“…The branched-chain hexose skeleton underlying the structure of the inhibitor arises by an intramolecular rearrangement of FBP yielding HBP (5). This reaction takes place in the chloroplast and an equilibrium between HBP and FBP at a ratio of approximately of 1:10 has been found (1). With leaves of a primrose, (Primula clusiana Tausch) metabolic dephosphorylation of HBP has been demonstrated resulting in a mixture of hamamelose-2'-and -5-P as well as of free hamamelose (5).…”

Section: Natural Chloroplast Constituents Related Tomentioning

confidence: 99%

An Assessment of the Rubisco Inhibitor

Beck

Scheibe²,

Reiner³

1989

Plant Physiol.

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2-Carboxyarabinitol-1-phosphate, the noctumal inhibitor of ribulose-1,5-bisphosphate carboxylase/oxygenase is identical with D-hamamelonic acid-21-phosphate. Reasoning is based on theoretical considerations as well as on mass spectra and 1H-and '3C-NMR spectra of the phosphate-free compounds. D-Hamamelonic acid-21-phosphate is interpreted as a metabolic derivative of D-hamamelose-21,5-bisphosphate which originates in the chloroplast from fructose-1,6-bisphosphate. A simple method for the synthesis of the inhibitor is suggested.

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“…Hamamelitol occur-s in leaves of 44% of angiospenrrs examined, with r-elatively high levels of 6-7 ^mol g"' fVesh weight (c. 4% by dry weight) in leaves of Hedera helix (English ivy; Moore, Hackett & Seemann 1995a). Har-nanielitol is probably forr-r-red within the leaf by reduction of han-ramelose, while the br-anched-chain str-uetur-e of hamamelose is formed by a rearrangement of fruetose-bisphosphate (Beck 1982).…”

mentioning

confidence: 99%

“…Hatiiatnelitol is thought to occur outside the chlot-oplast (Beck 1982), but its pt-ecise locatioti i.s unktiown. Beck & Hopf (1990) have suggested that hatnatnelitol tnay futiction as a coti-tpatible solute, in which case it tnust occur at substantial levels in the tnesophyll cytoplastn.…”

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confidence: 99%

Function of leaf hamamelitol as a compatible solute during water stress treatment of Hedera helix L.

Moore

Talbot

Seemann

1997

Plant Cell & Environment

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Hamamelitol is an unasual branched-chain sugar alcohol previously suggested to function as a leaf compatible solute. In tbis study, we bave examined tbe leaf metabolism and intracellular compartmentalization of bamamelitol and otber soluble sugars during long-term water stress treatment o[ Hedera helix (Englisb ivy). Total leaf bamamelitol content was relatively low in greenbouse control plants, but increased 2-lbld during water stress treatment to levels approaching tho.se observed in fieldgrown plants (6-7 /jmol g"' fresb weigbt). Using density gradient fractionation witb non-aqueous solvents, we sbowed tbat bamamelitol occurs primarily in tbe cytoplasm and vacuoles of leaf mesopbyll cells. During water stress treatment most of tbe increase in leaf bamamelitol occurred in tbe mesopbyll cytoplasm, compensating osmotically for a decrease in cytoplasmic sucrose concentration. The maximum concentration of cytoplasmic bamamelitol was 155 mol m"^ and occurred in field-grown plants. Labelling experiments sbowed tbat bamamelitol is slowly syntbesized from '''COj in leaves of //. helix., but is very long-lived (estimated t^^ ot 4 years). Togetber, tbese data indicate tbat bamamelitol probably functions during long-term stress conditions as an osmotically active, compatible solute in plant leaves. We sugge.st that tbe signal for enhanced accumulation of hamamelitol during the water .stress treatment was initiated by decreased plant growtb and increased leaf sucrose bydrolysis.

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Branched-Chain Sugars

Cited by 6 publications

References 132 publications

Conversion of D-Hamamelose into 2-Carboxy-D-arabinitol and 2-Carboxy-D-arabinitol 1-Phosphate in Leaves of Phaseolus vulgaris L.

Conversion of D-Hamamelose into 2-Carboxy-D-arabinitol and 2-Carboxy-D-arabinitol 1-Phosphate in Leaves of Phaseolus vulgaris L.

An Assessment of the Rubisco Inhibitor

Function of leaf hamamelitol as a compatible solute during water stress treatment of Hedera helix L.

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