Lipid-Linked Sugars As Intermediates in The Biosynthesis of Complex Carbohydrates in Plants

Lezica, Rafael Pont; Daleo, Gustavo Raúl; Dey, Prakash M.

doi:10.1016/s0065-2318(08)60081-5

Cited by 9 publications

(2 citation statements)

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“…Long-chain (C 90 -100 ) dolichyl phosphates are present in higher eukaryotes, both animals [2] and plants [3], whereas shorter-chain (C SS -8S ) compounds are found in lower eukaryotes and in cell-surface glycoprotein-producing bacteria as, for example, Hatobacterium sp. [4] and Bacillus sp.…”

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confidence: 99%

“…A few physicochemical studies demonstrated that dolichyl and polyprenyl phosphates have a destabilizing effect on membrane structure [11], which suggests another possible physiological role of polyisoprenyl phosphates in the activity and function of biological membranes. Given the key role of polyprenyl and dolichyl phosphates in nature and the fact that, in some organisms [5,3], both types of polyisoprenyl phosphates seem to operate (for example, Bacillus sp. utilizes a C ssundecaprenyl-P for the biosynthesis of cell-wall polysaccharides and a Css-dolichyl-P for the biosynthesis of a glycoprotein), it is important to develop new sensitive and informative methods for the structural determination of these compounds.…”

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Desorption chemical ionization tandem mass spectrometry of polyprenyl and dolichyl phosphates

Wolucka¹,

Rozenberg²,

Hoffmann³

et al. 1996

J. Am. Soc. Mass Spectrom.

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Negative-ion desorption chemical ionization (DCI) tandem mass spectrometry was applied to the analysis of nanomole quantities of semisynthetic polyisoprenyl phosphates, the chain length of which ranged from 7 to 20 isoprene units. The DCI spectrum of all the compounds tested show the presence of independently generated ions [M-HPO3-H](-), [M-H3PO2-H](-) and [M-H3PO4-H](-) resulting from the loss of a part of or the entire phosphate group of a polyisoprenyl-P. In tandem mass spectrometry, the [M-H3PO4-H](-) fragment produces series of ions 68 mass units apart, indicative of the polyisoprenoid nature of a compound. Studies with deuterated and α-saturated polyisoprenyl phosphates demonstrated that fragmentations of the [M-H3PO4-H](-) ion proceed from both ends (α and ω) of a polyisoprenoid chain and may occur at either allylic (A) or vinylic (V) sites. Fragments of masses equal to [n×68 - 1] and [n×68 - 13] (where n is the number of isoprene units and 3≤n is less than the total number of isoprene residues within a polyisoprenoid chain) comprise the αA and ωV series, respectively, and represent the most abundant ions in tandem mass spectra of the [M-H3PO4-H](-) fragment of polyprenyl phosphates, α-Saturated dolichyl phosphates can be distinguished easily from corresponding polyprenyl phosphates not only on the basis of a 2-u shift of the [M-H3PO4-H](-) ion and the α series of fragments, but also because of the presence of an additional (A+14) series of ions 14 u heavier than fragments resulting from the allylic cleavages of an α-saturated polyisoprenoid chain. Possible mechanisms of the collision-induced dissociation reactions of polyprenyl phosphates are discussed.

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confidence: 99%

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Desorption chemical ionization tandem mass spectrometry of polyprenyl and dolichyl phosphates

Wolucka¹,

Rozenberg²,

Hoffmann³

et al. 1996

J. Am. Soc. Mass Spectrom.

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ChemInform Abstract: Lipid‐Linked Sugars as Intermediates in the Biosynthesis of Complex Carbohydrates in Plants

Lezica

Daleo

1987

ChemInform

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Detection of the lipid‐linked precursor oligosaccharide of N‐linked protein glycosylation in Drosophila melanogaster

et al. 1991

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The presence of a glycan of the same molecular size as the lipid linked precursor oligosaccharide (Glc,Man,GlcNAc,) of the N-linked protein glycosylation pathway in mammalian cells has been detected in a glycolipid fraction of cultured Drosophila ntefanogaster cells. Oligosaccharide sequencing studies were consistent with the existence of a glucosylated high mannose containing structure, which may be the common precursor for N-linked protein glycosylation in insect cells.N-Linked protein glycosylation; Glycolipid; Lipid-linked precursor oligosaccharide; Metabolic labelling: Drosophila n~ekogonasrer 1, INTRODUCTIONA consensus for the major pathway of N-linked glycosylation in vertebrates has been established /l]. This pathway involves the synthesis of the precursor oligosaccharide, GlucoseJvIannoseJV-Acetylglucosamine, (Glc,Man,GlcNAc2), attached to dolichol, a long chain isoprenoid alcohol. The glpan is transferred en-Hoc to nascent polypeptide chains in the endoplasmic reticulum. The precursor oligosaccharide is processed to give the diversity of final carbohydrate structures seen in mature glycoproteins. It is apparent that the initial synthesis and transfer reaction are the same in all eukaryotes analysed except for Trypanosoma cruzi, Crithidia fasciculata and Leishmania mexicana [2]. The precursor oligosaccharide transferred onto proteins in these organisms lacks the three glucoses. Non-vertebrate eukaryotes also differ in the processing of the precursor oligosaccharides 12-41.In vertebrates processing is begun by the removal of the three glucoses from the precursor oligosaccharide by two enzymes. These are cl-glucosidase 1 (EC. 32.106) which removes the terminal a-l-2 linked glucose, and ol-glucosidase II (EC. 3.2.106, mannosyl-oligosaccharide glucosidase) which then removes the two remaining a-1-3 linked glucoses [1,4]. Our objective is to identify similar processing enzymes in Drosophila melanogaster. However, in the light of observations such as those on the three organisms lacking three terminal glucoses in their precursor, it is necessary to proCorrespondence address: G,F. Parker, Genetics Laboratory, Department of Biochemistry, University of Oxford, South Parks Road, Oxford, OX1 3QU, UK. 58vide biochemical evidence for the existence of a glucosylated precursor oligosaccharide in this organism. MATERIALS AND METHODSBio-Gel P-4, Dowex AGSOXl2-100, Dowex AG3-X4A and Chelex 100 were obtained from Rio-Rad laboratories, radioactive mannose ([2-'I-I]mannose 16.3 Ci/mmol) was purchased from Amersham Ltd, amino acids and organic buffers rep ccl1 culture were purchased from Sigma. QAE-Sephadex A-25 was obtained from Pharmacia Ltd. (Milton Keynes, UK). Foetal calf serum was supplied by Globepharm (Surrey, UK). Glutamine and trypsin were purchased from Gibco (Gibco/BRL, UK). Yeast extract powder was from Lab M, chloroform and methanol were 'analar' grade supplied by BDH.Porcine liver ce-glucosidase I was prepared from detergent extracts of isolated microsomes and purified using carboxypentyl deoxynojirimicyn-aga...

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Lipid-Linked Sugars As Intermediates in The Biosynthesis of Complex Carbohydrates in Plants

Cited by 9 publications

References 260 publications

Desorption chemical ionization tandem mass spectrometry of polyprenyl and dolichyl phosphates

Desorption chemical ionization tandem mass spectrometry of polyprenyl and dolichyl phosphates

ChemInform Abstract: Lipid‐Linked Sugars as Intermediates in the Biosynthesis of Complex Carbohydrates in Plants

Detection of the lipid‐linked precursor oligosaccharide of N‐linked protein glycosylation in Drosophila melanogaster

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