PHOTOSYNTHESIS OF GALACTOLIPIDS - Journal of the American

A. A. Benson, R. Wiser, R. A. Ferrari, and J. A. Miller. J. Am. Chem. Soc. , 1958, 80 (17), pp 4740–4740. DOI: 10.1021/ja01550a079. Publication Date...
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The molecule may be considered as built of four thentic samples generously provided by Professor main planar or approximately planar groups, p - 13. E. Carter. The glyceryl galactotrioside was methyl-thiophenyl, prolyl, peptide pyrrolidine found in a chromatographic position (Rf= 0.50 and carboxyl, all of which tend t o lie a t approxi- in phenol-water and Rf= 0.14 in butanol-propionic mately right angles to one another. I n the case acid-water2) characteristic of L: third member of of the proly! ring i t would appear that the carbon the homologous series of galactosyl glycerides. atom opposite the N-C, bond does not show any Hydrolysis by thirty minutes in 3 AT hydrochloric tendency to occupy alternate sites as noted by acid a t 100’ of ihe uniformly labeled unknown Leung and Marsh in the analysis of leucylprolyl- formed during eight days of photosynthesis gave glycine monohydrate.l% Neither does it maintain galactose and glycerol in an activity ratio of 6.1 to the position observed in prolinelo or hydroxypro- 1, thus indicating that there are three galactose line,” Le., trans with respect to the carboxyl group. units bound tn J. monoglyceride in the original I n this compound i t appears to have swung to the lipid. same side as the peptide C=O, providing further The only precursor a\ ailable in appreciab!e cvidence of the flexibility of the pyrrolidine ring concentration in Chlorella for biosynthesis of these system in the prolyl group. $ycolipids is uridine diphosphate galactose.‘a8 CHENXCAL PIiYsres SECTION A . F.EEECHAM Biosynthesis of galxtosyl glycerides IS probably analogous to that of the uridine diphosphate galac~ I V I S I O h ’OF INDUSTRIAL CHEhlISl R\’ C. S. I R. 0. J. 1‘RIDRICIISONS tose-mediated saccbaride syntheses. XELBOUKNE, AUSTRALIA A. IvlcL. MATXIESON We are indebted to N r . M. S. Brown for valuable RECEIVED h 3 A Y 5 , 1958 assistance. This work was supported by the Atomic Energy Commission and the Pennsylvania Agricultural Experinient Station. PHOTOSYNTHESIS OF GALACTOLIPIDS (7) J G Du‘hanan, V €3. Lynch, A. A. Beuson, U. 1’. Bradley nnd Sir: RI. Calvin, J . B i d Chsm., 203, 935 (1055). An appreciable portion of the products of brief ( 8 ) V. Ginsburg. F. K. ftumpf and W. 2. Hassid, rbrd., 223, 977 photosynthesis in Cl4OS is lipid in nature.I Chro- (1966). (9) E. 1’. Neufeld, V. Ginsburg, E. W Putrnan, D. Fanshier and matograms of these products exhibit several separable lipids2 which had been assumed t o be fatty W. 2 Hassid, Arch. Brochem. Riophys., 69, GO2 (1957). or AGRICULTURAL Air) A PA BENSON acid-labeled phosphatides. Eowever, me wish to UEPARTM~~:;T CHEMI5TRY R. WISER report that the phosphatides constitute but a frac- BIOLOGICAL PENXSYLVASIA STATE U N I V ~ R S I T Y R. A. FERRARI tion of these labeled products. We have examined UNIVEKSITY PARK, PENMYLVANIA J. -4 MILLER the lipids of Chlorellar and find that the glycolipid f