L-Phenylalanine (13C9)

Catalog Number	ACM439685117
CAS	439685-11-7
Molecular Weight	174.12
Molecular Formula	13C9H11NO2
Melting Point	270-275 °C (518-527 °F)
Purity	98%
Appearance	White to off-white Crystalline
Chemical Formula	*C6H5*CH2*CH(NH2)*COOH
Isotopic Enrichment	99 atom % 13C
pH	5.0-7 at 16.5 g/L at 25 °C (77 °F)
CAS (Unlabeled)	63-91-2
Synonyms (Unlabeled)	(S)-2-Amino-3-phenylpropionic acid

Case Study

Metabolism Study of L-Phenylalanine into Aromatic Volatiles in Melon Fruit

Gonda I, et al. Phytochemistry, 2018, 148, 122-131.

This work demonstrated the metabolism of isotope-labeled L-phenylalanine (13C9-L-phe) into aromatic volatiles in melon fruit. It was found that 13C9-L-phe was converted into more than 20 volatile compounds.
· Metabolism of 13C9-L-phenylalanine
Compounds such as phenylpropanes, phenylpropenes, and benzenoids are believed to be synthesized through the established phenylpropanoid pathway, which involves phenylalanine ammonia lyase (PAL), with (E)-cinnamic acid serving as a crucial intermediate. In contrast, phenethyl derivatives appear to originate from L-phenylalanine through a distinct biosynthetic pathway that does not include (E)-cinnamic acid or PAL.
· Stable Isotope Feeding Experiments
Strips of melon rind weighing approximately 0.2 g of fresh weight were cut from mature fruits and placed in sterile Petri dishes. Each strip was gently treated with 100 ml of either a 5 mM isotopically labeled (13C9-L-phe) or non-labeled L-phenylalanine solution. The dishes were then covered and incubated for 6 hours at room temperature. After incubation, the strips were thoroughly rinsed, frozen in liquid nitrogen, and ground into a fine powder using a grinder. For volatile sampling, 1 g of the ground tissue was transferred to a 10 ml glass vial containing 0.7 g of solid NaCl and 2 ml of a 20% (w/v) NaCl solution, which included 0.2 mg of 2-heptanone as an internal standard.

13C9-L-Phenylalanine for the Biosynthesis Study of Bifunctional Ammonia Lyase (PTAL)

Barros J, et al. Nature plants, 2016, 2(6), 1-9.

In this work, phenylpropanoid biosynthesis was isotopically traced using 13C9-labeled precursors, and a BdPTAL1 RNA interference (RNAi) line of Brachypodium distachyon was generated to study the effect of disruption of PTAL expression on cell wall lignification. The results showed that the TAL activity of BdPTAL1 can provide nearly half of the total lignin deposited in Brachypodium and preferentially performs S-lignin and wall-bound coumaric acid biosynthesis.
13C9-labeled precursors for isotopic tracing
· Brachypodium plants were first grown in medium containing 13C9-labeled L-Phe or L-Tyr, harvested at 10 and 30 days after germination, and their lignin composition was analyzed by thioacidolysis gas chromatography-mass spectrometry (GC-MS).
· Only plants fed with labeled precursors exhibited M+7 monolignol-derived fragments. Consistent with their lignification level and labeling method, label incorporation into monolignols was higher in roots than stems. Incorporation was similar between 10- and 30-day-old plantlets. L-Phe was preferentially incorporated into H-units of root lignin at both stages, while L-Tyr was better incorporated into S-units. As expected due to lack of TAL activity, 15-day-old Arabidopsis roots incorporated only L-Phe into lignin.
· It was estimated that 100 mg of B. distachyon stem lignin contains, on average, 4 mg of H-units (3 mg from L-Phe, 1 mg from L-Tyr), 41 mg of G-units (24 mg from L-Phe, 17 mg from L-Tyr), and 55 mg of S-units (27 mg from L-Phe, 28 mg from L-Tyr).
Unlike dicots, grasses have significant amounts of esterified 4-coumaric acid (4CA) and ferulate in cell walls. 13C9-label was detected in these molecules, with L-Tyr being incorporated more efficiently into 4CA than ferulate.

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L-Phenylalanine (13C9) (439685-11-7)

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