N-α-Carbobenzoxy-L-glutamic acid N-γ-ethylamide
Need Assistance?
  • US & Canada:
    +
  • UK: +

N-α-Carbobenzoxy-L-glutamic acid N-γ-ethylamide

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
CBZ-Amino Acids
Catalog number
BAT-005988
CAS number
95082-77-2
Molecular Formula
C15H20N2O5
Molecular Weight
308.33
N-α-Carbobenzoxy-L-glutamic acid N-γ-ethylamide
IUPAC Name
(2S)-5-(ethylamino)-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid
Synonyms
Z-Glu(NHEt)-OH; Z-Gln(Et)-OH; N-α-Carbobenzoxy-N-γ-ethyl-L-glutamine
InChI
InChI=1S/C15H20N2O5/c1-2-16-13(18)9-8-12(14(19)20)17-15(21)22-10-11-6-4-3-5-7-11/h3-7,12H,2,8-10H2,1H3,(H,16,18)(H,17,21)(H,19,20)/t12-/m0/s1
InChI Key
PIHNKRMQCZEQMR-LBPRGKRZSA-N
Canonical SMILES
CCNC(=O)CCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
1. Kokumi substances, enhancers of basic tastes, induce responses in calcium-sensing receptor expressing taste cells
Yutaka Maruyama, Reiko Yasuda, Motonaka Kuroda, Yuzuru Eto PLoS One. 2012;7(4):e34489. doi: 10.1371/journal.pone.0034489. Epub 2012 Apr 12.
Recently, we reported that calcium-sensing receptor (CaSR) is a receptor for kokumi substances, which enhance the intensities of salty, sweet and umami tastes. Furthermore, we found that several γ-glutamyl peptides, which are CaSR agonists, are kokumi substances. In this study, we elucidated the receptor cells for kokumi substances, and their physiological properties. For this purpose, we used Calcium Green-1 loaded mouse taste cells in lingual tissue slices and confocal microscopy. Kokumi substances, applied focally around taste pores, induced an increase in the intracellular Ca(2+) concentration ([Ca(2+)](i)) in a subset of taste cells. These responses were inhibited by pretreatment with the CaSR inhibitor, NPS2143. However, the kokumi substance-induced responses did not require extracellular Ca(2+). CaSR-expressing taste cells are a different subset of cells from the T1R3-expressing umami or sweet taste receptor cells. These observations indicate that CaSR-expressing taste cells are the primary detectors of kokumi substances, and that they are an independent population from the influenced basic taste receptor cells, at least in the case of sweet and umami.
2. Involvement of the calcium-sensing receptor in human taste perception
Takeaki Ohsu, Yusuke Amino, Hiroaki Nagasaki, Tomohiko Yamanaka, Sen Takeshita, Toshihiro Hatanaka, Yutaka Maruyama, Naohiro Miyamura, Yuzuru Eto J Biol Chem. 2010 Jan 8;285(2):1016-22. doi: 10.1074/jbc.M109.029165. Epub 2009 Nov 5.
By human sensory analyses, we found that various extracellular calcium-sensing receptor (CaSR) agonists enhance sweet, salty, and umami tastes, although they have no taste themselves. These characteristics are known as "kokumi taste" and often appear in traditional Japanese cuisine. Although GSH is a typical kokumi taste substance (taste enhancer), its mode of action is poorly understood. Here, we demonstrate how the kokumi taste is enhanced by the CaSR, a close relative of the class C G-protein-coupled receptors T1R1, T1R2, and T1R3 (sweet and umami receptors). We identified a large number of CaSR agonist gamma-glutamyl peptides, including GSH (gamma-Glu-Cys-Gly) and gamma-Glu-Val-Gly, and showed that these peptides elicit the kokumi taste. Further analyses revealed that some known CaSR agonists such as Ca(2+), protamine, polylysine, L-histidine, and cinacalcet (a calcium-mimetic drug) also elicit the kokumi taste and that the CaSR-specific antagonist, NPS-2143, significantly suppresses the kokumi taste. This is the first report indicating a distinct function of the CaSR in human taste perception.
Online Inquiry
Verification code
Inquiry Basket