H-β-(2-Furyl)-L-alanine
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H-β-(2-Furyl)-L-alanine

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Category
L-Amino Acids
Catalog number
BAT-005560
CAS number
127682-08-0
Molecular Formula
C7H9NO3
Molecular Weight
155.16
H-β-(2-Furyl)-L-alanine
IUPAC Name
(2S)-2-amino-3-(furan-2-yl)propanoic acid
Synonyms
3-L-Ala(2-furyl)-OH
Appearance
White to off-white powder
Purity
≥ 99% (Chiral purity)
Density
1.3±0.1 g/cm3
Boiling Point
284.1±30.0 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C7H9NO3.ClH/c8-6(7(9)10)4-5-2-1-3-11-5;/h1-3,6H,4,8H2,(H,9,10);1H/t6-;/m0./s1
InChI Key
LWMGRXJXMDWFGB-RGMNGODLSA-N
Canonical SMILES
C1=COC(=C1)CC(C(=O)O)N.Cl
1.How to spoil the taste of insect prey? A novel feeding deterrent against ants released by larvae of the alder leaf beetle, Agelastica alni.
Hilker M1, Häberlein C, Trauer U, Bünnige M, Vicentini MO, Schulz S. Chembiochem. 2010 Aug 16;11(12):1720-6. doi: 10.1002/cbic.201000130.
Chemical defense of leaf beetle larvae (Chrysomelidae) against enemies is provided by secretions containing a wide range of deterrent compounds or by unpalatable hemolymph constituents. Here we report a new, very strong feeding deterrent against ants released by larvae of the alder leaf beetle Agelastica alni when attacked. The larvae release a defensive fluid from openings of pairwise, dorsolaterally located tubercles on the first to the eighth abdominal segments. The fluid, consisting of hemolymph and probably a glandular cell secretion, has previously been shown to contain a very stable, non-volatile feeding deterrent. The major deterrent component was isolated by repeated HPLC separation and analyzed by NMR and MS. The compound proved to be gamma-L-glutamyl-L-2-furylalanine (1), a novel dipeptide containing the unusual amino acid L-2-furylalanine. This amino acid, although synthetically well known, has not previously been reported from natural sources.
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