H-MET-TRP-OH
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H-MET-TRP-OH

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H-MET-TRP-OH is an incomplete breakdown product of protein digestion or protein catabolism. It is a non-competitive inhibitor of angiotensin-1 converting enzyme (ACE), with an IC50 of 9.8 μM.

Category
Peptide Inhibitors
Catalog number
BAT-015409
CAS number
60535-02-6
Molecular Formula
C16H21N3O3S
Molecular Weight
335.42
H-MET-TRP-OH
IUPAC Name
(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
Synonyms
Methionyltryptophan; L-Methionyl-L-tryptophan; Met-trp; L-Met-L-Trp; N-L-methionyl-L-tryptophan
Purity
95%
Density
1.327±0.06 g/cm3
Boiling Point
667.9±55.0 °C at 760 mmHg
Sequence
H-Met-Trp-OH
Storage
-15°C
InChI
InChI=1S/C16H21N3O3S/c1-23-7-6-12(17)15(20)19-14(16(21)22)8-10-9-18-13-5-3-2-4-11(10)13/h2-5,9,12,14,18H,6-8,17H2,1H3,(H,19,20)(H,21,22)/t12-,14-/m0/s1
InChI Key
XYVRXLDSCKEYES-JSGCOSHPSA-N
Canonical SMILES
CSCCC(C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O)N
1.Conformations and properties of the L-tryptophyl-containing peptides in solution, depending on the pH--theoretical study vs. experiments.
Ivanova BB1, Spiteller M. Biopolymers. 2010 Aug;93(8):727-34. doi: 10.1002/bip.21437.
The conformational preference and electronic properties of three L-tryptophyl-containing dipeptides, i.e., glycyl-L-tryptophane (H-Gly-Trp-OH), L-alanyl-L-tryptophane (H-Ala-Trp-OH), and L-methionyl-L-tryptophane (L-Met-Trp-OH) in solution depending on the pH of the media are studied both theoretically and experimentally. The effect of the protonation of the COO(-) and deprotonation of the NH3+ as well as the alkaline hydrolysis of the amide fragment in a strong basic media on the electronic spectra are discussed. Ab initio and density functional theory (DFT) methods as well as the time-dependent DFT (TD-DFT) method as a function of the basis set are performed with a view to obtain the geometry and electronic properties of all of the species as well as the intermediate, obtained in the alkaline hydrolysis mechanism.
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