The distribution of phospholipase B in mammalian tissues

Marples, Elizabeth A.; Thompson, R. H. S.

doi:10.1042/bj0740123

Cited by 77 publications

(14 citation statements)

References 14 publications

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“…In addition, it has been shown that brain tissue contains other enzymes, which can convert lysolecithin into the nontoxic glycerylphosphorylcholine (Marples & Thompson 1960) by splitting off the single fatty acid present in the lysolecithin molecule, or which can add on a second fatty acid to lysolecithin to re-convert it to lecithin .…”

Section: Phospholipid Metabolismmentioning

confidence: 99%

A Biochemical Approach to the Problem of Multiple Sclerosis

Thompson

1966

Proceedings of the Royal Society of Medicine

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Section: Phospholipid Metabolismmentioning

confidence: 99%

A Biochemical Approach to the Problem of Multiple Sclerosis

Thompson

1966

Proceedings of the Royal Society of Medicine

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“…138 of 2 results in 1,2,5,6-tetrabenzyl-~-mannitol (3) which is converted to 1,2-dibenzyl-glyceraldehyde (4) by treatment with lead tetraacetate. Reduction of 4 with lithium aluminium hydride leads to 1,2-dibenzyl-glycerol (3, and subsequent esterification with palmitoylchloride yields 1,2-dibenzy1-3-palmitoyl-glycerol (6). Monodebenzylation of 6 by catalytic hydrogenolysis results in an equimolar mixture of 2-benzyl-3-palmitoyl-glycerol (7) and 1-benzyl-3-palmitoyl-glycerol (8).…”

mentioning

confidence: 99%

Synthesen von Cholinphosphatiden, VI¹⁾ 3‐Palmitoyl‐glycerin‐1‐phosphorylcholin (D‐α‐Lysolecithin) und dessen Unwirksamkeit als Substrat für Acyltransferasen (Lecithin‐Synthese)

Eibl

Westphal

Bosch

et al. 1970

Justus Liebigs Ann. Chem.

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Als Modellsubstanzen fur biologische Untersuchungen sind einheitliche, konfigurativ eindeutige Lysolecithine von allgemeinem Interesse. Wir beschreiben erstmals die Synthese eines 3-Acyl-glycerin-I-phosphorsaurecholinesters (B). 3.4-Isopropyhden-~-mannit (1) wird zur Tetrabenzyl-Verbindung 2 benzyliert. Saure Hydrolyse von 2 ergibt 1.2.5.6-Tetrabenzyl-D-mannit (3), der mittels Bleitetraacetat zu 1.2-Dibenzyl-glycerinaldehyd (4) gespalten wird.Reduktion von 4 mit Lithiumalanat fuhrt zum 1.2-Dibenzyl-glycerin (3, das durch Veresterung mit Palmitinsaurechlorid das 3-Palmitoyl-Derivat 6 liefert. Aus 6 erhalt man bei der katalytischen Hydrogenolyse 2-Benzyl-und 1 -Benzyl-3-palmitoyl-glycerin (7 bzw. 8), die chromatographisch getrennt werden. Die Phosphorylierung von 7 mittels P-Brom-athyldichlorphosphat und die nachfolgende Behandlung mit Trimethylamin ergeben 3-Palmitoyl-2-benzyl-glycerin-1 -phosphorylcholin (9), das durch katalytische Hydrogenolyse in 3-Palmitoyl-glycerin-I-phosphorylcholin (10) umgewandelt wird. -Das so dargestellte D-E-LYSOlecithin erweist sich im Gegensatz zu 1 -Palmitoyl-glycerin-3-phosphorylcholin (L-a-Lysolecithin) nicht als Substrat fur Acyl-CoA : Acylglycerinphosphorylcholin-Acyltransferasen, Synthesis of Choline Phosphatides, VIL). 3-Palmitoyl-glycerol-I-phosphorylcholine (D-a-LySOlecithin) and its Inactivity as Substrate for AcyltransferasesEnzyme reactions controlling the content of the strong lytic agent lysolecithin (monoacylglycerol-3-phosphoryIcholine) in cell membranes, i. e. by degradation or by reacylation, are of great importance for the living cell. Lysolecithins, well defined with respect to configuration and structure, can be used as substrates for studying the metabolic fate of these compounds in membranes. Five of the six theoretically possible isomers of lysolecithin have been prepared by De Haas and Van Deenen (1965). -In this paper the synthesis of the hitherto unknown 3-acyl-glycerol-I-phosphorylcholine (B) is described. 3,4-lsopropylidene-~-mannitol (1) has been benzylated to give 1,2,5,6-tetrabenzyl-3,4-isopropylidene-~-mannitol (2). Acid hydrolysis

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“…Lysophosphotlpase.--Enzymic cleavage of the fatty acid ester linkage of monoacyl phosphoglycerides is an important reaction in phospholipld catabolism, and thls activity is widely distributed, e.g., in many animal tissues (321). Since monoacyl phosphoglycerides, prepared by phospholipase 2 from snake-venom, have been used as substrate, Reaction 3 (Scheme 4) involved.…”

Section: Lecithin + Cholesterol --* 1-acyl-glycero-3-phosphoryl Cholimentioning

confidence: 99%

Phosphoglycerides and Phospholipases

Deenen¹,

Haas²

1966

Annu. Rev. Biochem.

113

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Although this review is confined to some chemical and biochemical as pects of phospholipids, the number of relevant publications not included ex ceeds that of the list of references. In addition to recent reviews on chemical composition (1), chemical synthesis (2, 3), and metabolism of phospholipids (4-7), and on membrane structures (8) cited here, reference will be made at the beginning of several sections of this chapter to more specialized surveys.At present, naturally occurring phospholipids are denoted as L-a-com pounds (9), D-l-derivatives (10, 11), and L-3-compounds (4). This situation creates confusion which may be avoided by adoption of the system of abso lute stereochemical designation proposed by Hirschmann (12). This stereo specific system of numbering of the carbon atoms of glycerol and other com pounds which possess reflective but not rotational symmetry will be followed in this review.

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The distribution of phospholipase B in mammalian tissues

Cited by 77 publications

References 14 publications

A Biochemical Approach to the Problem of Multiple Sclerosis

A Biochemical Approach to the Problem of Multiple Sclerosis

Synthesen von Cholinphosphatiden, VI¹⁾ 3‐Palmitoyl‐glycerin‐1‐phosphorylcholin (D‐α‐Lysolecithin) und dessen Unwirksamkeit als Substrat für Acyltransferasen (Lecithin‐Synthese)

Phosphoglycerides and Phospholipases

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The distribution of phospholipase B in mammalian tissues

Cited by 77 publications

References 14 publications

A Biochemical Approach to the Problem of Multiple Sclerosis

A Biochemical Approach to the Problem of Multiple Sclerosis

Synthesen von Cholinphosphatiden, VI1) 3‐Palmitoyl‐glycerin‐1‐phosphorylcholin (D‐α‐Lysolecithin) und dessen Unwirksamkeit als Substrat für Acyltransferasen (Lecithin‐Synthese)

Phosphoglycerides and Phospholipases

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Synthesen von Cholinphosphatiden, VI¹⁾ 3‐Palmitoyl‐glycerin‐1‐phosphorylcholin (D‐α‐Lysolecithin) und dessen Unwirksamkeit als Substrat für Acyltransferasen (Lecithin‐Synthese)