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608017

Sigma-Aldrich

L-Phenylalanine-13C9,15N

98 atom % 15N, 98 atom % 13C, 95% (CP), 97% (Chiral Purity)

Synonym(s):

(S)-2-Amino-3-phenylpropionic acid-13C9,15N, 13C and 15N Labeled L-phenylalanine, SILAC Amino Acid, Phenylalanine-UL-13C,15N

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About This Item

Linear Formula:
13C6H513CH213CH(15NH2)13CO2H
CAS Number:
Molecular Weight:
175.12
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.12

isotopic purity

98 atom % 13C
98 atom % 15N

Quality Level

Assay

95% (CP)
97% (Chiral Purity)

form

solid

optical activity

[α]25/D -33.0°, c = 1 in H2O

technique(s)

bio NMR: suitable

mp

270-275 °C (dec.) (lit.)

mass shift

M+10

SMILES string

[15NH2][13C@@H]([13CH2][13c]1[13cH][13cH][13cH][13cH][13cH]1)[13C](O)=O

InChI

1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1,10+1

InChI key

COLNVLDHVKWLRT-CMLFETTRSA-N

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General description

Phenylalanine is an aromatic nonpolar amino acid. Phenylalanine, tyrosine and tryptophan are three amino acids which can absorb ultraviolet radiation above 250nm. Degradation of phenylalanine results in the formation of acetoacetate and fumarate. Isotope labeled amino acids are required for the production of isotopically labeled proteins.

Application

L-Phenylalanine-13C9,15N has been used as a supplement in liquid growth culture of Nostoc species to study the involvement of noc operon (NoA biosynthesis operon) in NoA (nocuolin A) synthesis.

Packaging

This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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The cyanobacterial metabolite nocuolin a is a natural oxadiazine that triggers apoptosis in human cancer cells.
Voracova K, et al.
PLoS ONE, 12, e0172850-e0172850 (2017)
Harvey RA, et al.
Biochemistry (Lippincott's illustrated reviews) (2011)
Isotope labeling for solution and solid-state NMR spectroscopy of membrane proteins.
Verardi R, et al.
Advances in Experimental Medicine and Biology, 992, 35-62 (2012)
Incorporation of radioactive amino acids into proteins of the microsome fraction of guinea-pig liver in a cell-free system.
SIMKIN JL and WORK TS
The Biochemical Journal, 67, 617-624 (1957)
Garrett RH and Grisham CM
Biochemistry (2012)

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