Acyl phosphate naming

Acyl phosphates are named by citing the acyl group and adding the word phosphate. Tf an alkyl group is attached to one of the phosphate oxygens, it is identified after the name of the acyl group. In biological chemistry, acyl adenosyl phosphates are particularly common. 

Friedel-Crafts acylation reaction and,557-558 resonance in, 558 Acyl group, 557, 686 names of, 753 Acyl phosphate, 816 naming, 788 Acylation (aromatic), see... 

Acyl phosphates are named by citing the acyl group and adding the word phosphate. 

Lecithins and related phospholipids usually contain a saturated fatty acid in the C-l position but an unsaturated acid, which may contain from one to four double bonds, at C-2. Arachidonic acid is often present here. Hydrolysis of the ester linkage at C-2 yields a l-acyl-3-phosphoglycerol, better known as a Iysophosphatidylcholine. The name comes from the powerful detergent action of these substances which leads to lysis of cells. Some snake venoms contain phospholipases that form Iysophosphatidylcholine. Lysophosphatidic acid (l-acyl-glycerol-3-phosphate) is both an intermediate in phospholipid biosynthesis (Chapter 21) and also a signaling molecule released into the bloodstream by activated platelets.15... 

Glyceraldehyde-3-phosphate dehydrogenase has an essential cysteine residue in its active site. The enzyme forms a transient acyl compound with its substrate, glyceraldehyde 3-phosphate, (a) What is the general chemical name of the compound (b) Draw its likely structure. 

We have not told you the whole truth so far. Did you notice that SCoA in the structures had been replaced by CSR and that a mysterious ACP had crept into the enzyme names That was because these reactions actually happen while the growing molecule is attached as a thiol ester to a long side-chain on an acyl carrier protein (ACP). The long side-chain is closely related to CoA and is attached through a phosphate to a serine residue of the ACP. 

Alkyl halides are even less reactive than acyl halides, as indicated by the compilation of reaction rates of thiolate anions with various types of alkyl halides (282). Nevertheless, potentially useful affinity labels have been synthesized with alkyl halide substituents and have been shown to specifically inactivate several enzymes, albeit slowly the low reactivity of the alkyl halides may minimize nonspecific reaction. Adenosine 5 -(2-bromoethyl)phosphate has been characterized and reported to inactivate NAD -dependent isocitrate dehydrogenase (283). The 2 - and 3 -(2-bromoethyl)-AMP labels have also been synthesized, and model reactions of the bromoethyl-AMPs with cysteine, lysine, histidine, and tyrosine have been studied (284). More recently, esters of adenosine 5 -monophosphate have been prepared with ethyl, propyl, or hexyl moieties and bromo or chloro substituents at the w position (285). Yeast alcohol dehydrogenase exhibited enhanced inactivation by the hexyl derivative, but inactivation rates of other dehydrogenases were unremarkable. Two iodopropyl derivatives of cAMP have been described, namely, 1, A -(3-iodopropyleno)adenosine 3, 5 -cyclic monophosphate and 3 -0-(2-iodo-3-hydroxypropyl)adenosine 3, 5 -cyclic monophosphate the latter inactivates cAMP phosphodiesterase from human platelets, with a pseudo-first-order rate constant of 0.147 hr" (286). 

---