Fmoc-D-MePhe(4-OMe)-OH
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Fmoc-D-MePhe(4-OMe)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-008443
CAS number
193086-28-1
Molecular Formula
C26H25NO5
Molecular Weight
431.5
IUPAC Name
(2R)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-(4-methoxyphenyl)propanoic acid
Synonyms
Fmoc-D-N(Me)Tyr(Me)-OH; Fmoc-N-methyl-O-methyl-D-tyrosine; (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(4-methoxyphenyl)propanoic acid
Density
1.3±0.1 g/cm3
Boiling Point
623.9±55.0 °C at 760 mmHg
InChI
InChI=1S/C26H25NO5/c1-27(24(25(28)29)15-17-11-13-18(31-2)14-12-17)26(30)32-16-23-21-9-5-3-7-19(21)20-8-4-6-10-22(20)23/h3-14,23-24H,15-16H2,1-2H3,(H,28,29)/t24-/m1/s1
InChI Key
FRHSGZVWEBYEIV-XMMPIXPASA-N
Canonical SMILES
CN(C(CC1=CC=C(C=C1)OC)C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
1. Use of heterometallic alkali metal-magnesium aryloxides in ring-opening polymerization of cyclic esters
Rafał Petrus, Tadeusz Lis, Adrian Kowaliński Dalton Trans. 2022 Jun 13;51(23):9144-9158. doi: 10.1039/d2dt00731b.
In this work, alkali metal-magnesium aryloxides [Mg2Li2(MesalO)6] (1), [Mg2Na2(MesalO)6(THF)x] for x = 2 or 4 (2), and [Mg2K2(MesalO)6(THF)4] (3) derived from the reaction of MgnBu2 and nBuLi, metallic Na or K with methyl salicylate (MesalOH) were used as molecular platforms for the synthesis of new heterometallic compounds [Mg2Li2(EtsalO)6] (4), [MgK(EtsalO)3]n (5), [Mg6Na4Al(MesalO)13(OH)6(MesalOH)(THF)0.5(H2O)0.5] (6), and [Mg4Na2(MesalO)6(SalO)2(THF)4] (7) (EtsalOH = ethyl salicylate and SalOH2 = salicylic acid) by the reaction with EtOH, exposure to atmospheric moisture or addition of stoichiometric quantities of water. Compounds 4 and 5 were synthesized by transesterification of 1 and 3. Cluster 6 was formed haphazardly by exposing a THF solution of 2 derived using MgnBu2 stabilized with 1 wt% AlEt3 to atmospheric moisture. Compound 7 was synthesized by partial hydrolysis of 2. Homometallic magnesium aryloxide [Mg4(MesalO)4(OMe)4(HOMe)4] (8) was obtained by reaction of MgnBu2 and MesalOH in a methanol solution. The catalytic activity of 1-3 and 6-8 was investigated in the ring-opening polymerization (ROP) of L-lactide (L-LA) or benzaldehyde Tishchenko reaction.
2. Structure Elucidation of Urinary Metabolites of Fentanyl and Five Fentanyl Analogs using LC-QTOF-MS, Hepatocyte Incubations and Synthesized Reference Standards
Jakob Wallgren, et al. J Anal Toxicol. 2021 Jan 21;44(9):993-1003. doi: 10.1093/jat/bkaa021.
Fentanyl analogs constitute a particularly dangerous group of new psychoactive compounds responsible for many deaths around the world. Little is known about their metabolism, and studies utilizing liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-QTOF-MS) analysis of hepatocyte incubations and/or authentic urine samples do not allow for determination of the exact metabolite structures, especially when it comes to hydroxylated metabolites. In this study, seven motifs (2-, 3-, 4- and β-OH as well as 3,4-diOH, 4-OH-3-OMe and 3-OH-4-OMe) of fentanyl and five fentanyl analogs, acetylfentanyl, acrylfentanyl, cyclopropylfentanyl, isobutyrylfentanyl and 4F-isobutyrylfentanyl were synthesized. The reference standards were analyzed by LC-QTOF-MS, which enabled identification of the major metabolites formed in hepatocyte incubations of the studied fentanyls. By comparison with our previous data sets, major urinary metabolites could tentatively be identified. For all analogs, β-OH, 4-OH and 4-OH-3-OMe were identified after hepatocyte incubation. β-OH was the major hydroxylated metabolite for all studied fentanyls, except for acetylfentanyl where 4-OH was more abundant. However, the ratio 4-OH/β-OH was higher in urine samples than in hepatocyte incubations for all studied fentanyls. Also, 3-OH-4-OMe was not detected in any hepatocyte samples, indicating a clear preference for the 4-OH-3-OMe, which was also found to be more abundant in urine compared to hepatocytes. The patterns appear to be consistent across all studied fentanyls and could serve as a starting point in the development of methods and synthesis of reference standards of novel fentanyl analogs where nothing is known about the metabolism.
3. Vanadyl sulfates: molecular structure, magnetism and electrochemical activity
Anna Ignaszak, et al. Dalton Trans. 2018 Nov 13;47(44):15983-15993. doi: 10.1039/c8dt03626h.
Reaction of differing amounts of vanadyl sulfate with p-tert-butylthiacalix[4]areneH4 and base allows access to the vanadyl-sulfate species [NEt4]4[(VO)4(μ3-OH)4(SO4)4]·½H2O (1), [HNEt3]5[(VO)5(μ3-O)4(SO4)4]·4MeCN (2·4MeCN) and [NEt4]2[(VO)6(O)2(SO4)4(OMe)(OH2)]·MeCN (3·MeCN). Similar use of p-tert-butylsulfonylcalix[4]areneH4, p-tert-butylcalix[8]areneH8 or p-tert-butylhexahomotrioxacalix[3]areneH3 led to the isolation of [HNEt3]2[H2NEt2]2{[VO(OMe)]2p-tert-butylcalix[8-SO2]areneH2} (4), [HNEt3]2[V(O)2p-tert-butylcalix[8]areneH5] (5) and [HNEt3]2[VIV2VV4O11(OMe)8] (6), respectively. Dc magnetic susceptibility measurements were performed on powdered microcrystalline samples of 1-3 in the T = 300-2 K temperature range. Preliminary screening for electrochemical water oxidation revealed some activity for 2 with turnover frequency (TOF) and number (TON) of 2.2 × 10-4 s-1 and 6.44 × 10-6 (mmol O2/mmol cat.), respectively. The compound 3 showed an improved electrochemical activity in the presence of water. This is related to the increased number and the rate of electrons exchanged during oxidation of V4+ species, facilitated by protons generated in the water discharge process.
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