Z-O-tert-butyl-L-tyrosine methyl ester
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Z-O-tert-butyl-L-tyrosine methyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-003416
CAS number
5068-29-1
Molecular Formula
C22H27NO5
Molecular Weight
385.46
Z-O-tert-butyl-L-tyrosine methyl ester
IUPAC Name
methyl (2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
Synonyms
Z-O-tert-butyl-L-tyrosine methyl ester; Benzyloxycarbonyl-O-tert-butyl-tyrosin-methylester; Z-Tyr(TB)-OMe; N-Cbz-(O-tert-butyl)tyrosine methyl ester; N-benzyloxycarbonyl-O-tert-butyl-S-tyrosine methyl ester; Z-TYROSINE(TBU)-OME
Appearance
White powder
Purity
≥ 98% (TLC)
Density
1.138±0.060 g/cm3
Boiling Point
529.8±50.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C22H27NO5/c1-22(2,3)28-18-12-10-16(11-13-18)14-19(20(24)26-4)23-21(25)27-15-17-8-6-5-7-9-17/h5-13,19H,14-15H2,1-4H3,(H,23,25)/t19-/m0/s1
InChI Key
IPRNNTJYTNRIDM-IBGZPJMESA-N
Canonical SMILES
CC(C)(C)OC1=CC=C(C=C1)CC(C(=O)OC)NC(=O)OCC2=CC=CC=C2
1. Acridinium Ester Chemiluminescence: Methyl Substitution on the Acridine Moiety
Manabu Nakazono, Shinkoh Nanbu, Takeyuki Akita, Kenji Hamase J Oleo Sci. 2021;70(11):1677-1684. doi: 10.5650/jos.ess21186.
Methyl groups were introduced on the acridine moiety in chemiluminescent acridinium esters that have electron-withdrawing groups (trifluoromethyl, cyano, nitro, ethoxycarbonyl) at the 4-position on the phenyl ester. The introduction of methyl groups at the 2-, 2,7-, and 2,3,6,7-positions on the acridine moiety shifted the optimal pH that gave relatively strong chemiluminescence intensity from neutral conditions to alkaline conditions. 4-(Ethoxycarbonyl)phenyl 2,3,6,7,10-pentamethyl-10λ4-acridine-9-carboxylate, trifluoromethanesulfonate salt showed long-lasting chemiluminescence under alkaline conditions. Acridinium esters to determine hydrogen peroxide concentration at pH 7-10 were newly developed.
2. Stimulation of 125I-3-iodo-alpha-methyl-L-tyrosine uptake in Chinese hamster ovary (CHO-K1) cells by tyrosine esters
Naoto Shikano, et al. Nucl Med Biol. 2010 Feb;37(2):189-96. doi: 10.1016/j.nucmedbio.2009.10.003. Epub 2009 Nov 3.
Introduction: Transport of the amino acid analog (123)I-3-iodo-alpha-methyl-L-tyrosine, which is used in clinical SPECT imaging, occurs mainly via L-type amino acid transporter type 1 (LAT1; an amino acid exchanger). As LAT1 is highly expressed in actively proliferating tumors, we made a preliminary investigation of the effects of amino acid esters on enhancement of (125)I-3-iodo-alpha-methyl-L-tyrosine (IMT) uptake via LAT1 in Chinese hamster ovary (CHO-K1) cells. Methods: Because the sequence of the CHO-K1 LAT1 gene is not available, we confirmed LAT1 expression through IMT (18.5 kBq) uptake mechanisms using specific inhibitors. L-Gly, L-Ser, L-Leu, L-Phe, L-Met, L-Tyr, D-Tyr, L-Val and L-Lys ethyl/methyl esters were tested in combination with IMT. Time-course studies over a 3-h period were conducted, and the concentration dependence of L-Tyr ethyl and methyl esters (0.001 to 10 mM) in combination with IMT was also examined. For a proof of de-esterification of L- and D-Tyr ethyl and methyl esters in the cells (by enzymatic attack or other cause), the concentration of L- and D-Tyr was analyzed by high-performance liquid chromatography of the esters in phosphate buffer (pH 7.4) and cell homogenates at 37 degrees C or under ice-cold conditions. Results: Inhibition tests suggested that LAT1 is involved in IMT uptake by CHO-K1 cells. Co-administration of 1 mM of l-Tyr ethyl or methyl ester with IMT produced the greatest enhancement. The de-esterification reaction was stereo selective and temperature dependent in the homogenate. De-esterification kinetics were very fast in the homogenate and very slow in the phosphate buffer. Conclusions: The L-Tyr ethyl or methyl esters were the most effective enhancers of IMT uptake into CHO-K1 cells and acted by trans-stimulation of the amino acid exchange function of LAT1. This result suggests that de-esterification in the cells may be caused by enzymatic attack. We will use IMT and L-Tyr ethyl or methyl esters to examine LAT1 function in tumor cells or tissues in vivo.
3. O-Methylation of carboxylic acids with streptozotocin
Li-Yan Zeng, Yang Liu, Jiakun Han, Jinhong Chen, Shuwen Liu, Baomin Xi Org Biomol Chem. 2022 Jul 6;20(26):5230-5233. doi: 10.1039/d2ob00578f.
The clinically used DNA-alkylating drug streptozotocin (STZ) was investigated using a simple work-up as an O-methylating agent to transform various carboxylic acids, sulfonic acids and phosphorous acids into corresponding methyl esters, and did so with yields of up to 97% in 4 h at room temperature. Good substrate tolerance was observed, and benefited from the mild conditions and compatibility of the reaction with water.
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