EurekaMag.com logo
+ Site Statistics
References:
54,215,046
Abstracts:
30,230,908
PMIDs:
28,215,208
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on LinkedInFollow on LinkedIn

+ Translate

The obligatory role of phenyllactate in the biosynthesis of tropic acid



The obligatory role of phenyllactate in the biosynthesis of tropic acid



Phytochemistry (Oxford) 32(5): 1183-1187



Phenyl(1-14C)lactic acid and phenyl(2-3H)lactic acid were synthesized by conventional routes and fed in admixture (3H:14C ratio 10:1) to Datura stramonium via the roots. Hyoscine (scopolamine) and hyoscyamine were isolated and found to have essentially the same 3H:14C ratios as the precursor (8.5 and 10.15, respectively). Hydrolysis of hyoscyamine showed that all the activity was present in the tropic acid moiety. The tropic acid was converted to atropic acid and then cleaved by means of osmium tetroxide and sodium metaperiodate to yield formaldehyde containing all the tritium and phenylglyoxylic acid containing all the 14C, a result which shows that the tritium at C-2 of the phenyllactate precursor labelled tropic acid in the hydroxymethyl group. These findings show that phenyllactate is an obligatory intermediate in the biosynthesis of tropic acid and that the rearrangement of the side-chain takes place at the phenyllactate and not the phenylpyruvate level.

(PDF emailed within 0-6 h: $19.90)

Accession: 002524843

Download citation: RISBibTeXText

DOI: 10.1016/s0031-9422(00)95088-x



Related references

The rearrangement of phenyllactate in the biosynthesis of tropic acid. Phytochemistry (Oxford) 35(4): 935-939, 1994

The biosynthesis of tropic acid. Part 6. Enantioselective, intact incorporation of (R)-(+)-3-phenyllactic acid into the tropic acid ester alkaloids of Datura. Perkin Transactions 1 ( 4): 487-490, 1995

The biosynthesis of tropic acid part 2 incorporation of cinnamic acid 1 3 carbon 14 into tropic acid. Lloydia (Cincinnati) 38(6): 542-543, 1975

Synthesis of isotopically labelled 3 amino 2 phenylpropionic acid and its role as a precursor in the biosynthesis of tenellin and tropic acid. Journal of the Chemical Society Perkin Transactions I (10): 2537-2540, 1991

The biosynthesis of tropic acid: the stereochemical course of the mutase involved in hyoscyamine biosynthesis in Datura stramonium. Journal of the Chemical Society, Chemical Communications ( 2): 129-130, 1995

The biosynthesis of tropic acid: the (R)-D-phenyllactyl moiety is processed by the mutase involved in hyoscyamine biosynthesis in Datura stramonium. Journal of the Chemical Society, Chemical Communications ( 2): 127-128, 1995

Biosynthesis of tropic acid. Lloydia. 29: 381, 1966

Phenylalanine as the precursor of tropic acid and benzoic acid. On the biosynthesis of tropane alkaloids. III. Archiv der Pharmazie 296/68: 1-6, 1963

Biosynthesis of tropic acid. I. Incorporation of cinnamic acid-2-14C in Datura innoxia. Lloydia 39(1): 79-81, 1976

Biosynthesis of tropic acid part 1 incorporation of cinnamic acid 2 carbon 14 in datura innoxia. Lloydia (Cincinnati) 39(1): 79-81, 1976

The biosynthesis of tropic acid. Journal of Pharmacy and Pharmacology 30 Suppl: 82p-82p, 1978

Further studies on the biosynthesis of tropic acid. Jour Amer Chem Soc 84(23): 4507-4509, 1962

The breakdown of tropic acid in pseudomonas putida strain l part 1 utilization of various substrates the conversion of tropic acid into phenyl acetic acid. Biochimica Et Biophysica Acta: 204-211, 1971

The breakdown of tropic acid in Pseudomonas putida strain L. I. Utilization of various substrates; the conversion of tropic acid into phenylacetic acid. Biochimica et Biophysica Acta 230(2): 204-211, 1971