Fmoc-L-β-glutamic acid 5-tert-butyl ester
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Fmoc-L-β-glutamic acid 5-tert-butyl ester

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Fmoc-L-β-glutamic acid 5-tert-butyl ester is used in the synthesis of dimeric peptides targeting chemokine receptor CXCR4. It is also used to prepare chimeric (α/β + α)-peptide ligands for BH3-recognition cleft of Bcl-xl.

Category
Fmoc-Amino Acids
Catalog number
BAT-007572
CAS number
209252-17-5
Molecular Formula
C24H27NO6
Molecular Weight
425.48
Fmoc-L-β-glutamic acid 5-tert-butyl ester
IUPAC Name
(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
Synonyms
Fmoc-β-Glu(OtBu)-OH; Fmoc-L-β-homoaspartic acid 5-tert-butyl ester; Fmoc-beta-Hoasp(Otbu)-OH; Fmoc-beta-Glu(OtBu)-OH; Fmoc-L-beta-glutamic acid 5-tert-butyl ester; (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid; Fmoc-Glu(OtBu)-OH; (3R)-3-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-pentanedioic Acid 1-(1,1-Dimethylethyl) Ester
Appearance
White to off-white powder
Purity
≥ 95% (HPLC)
Density
1.232±0.06 g/cm3 (Predicted)
Melting Point
82-83 °C
Boiling Point
637.0±55.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C24H27NO6/c1-24(2,3)31-22(28)13-15(12-21(26)27)25-23(29)30-14-20-18-10-6-4-8-16(18)17-9-5-7-11-19(17)20/h4-11,15,20H,12-14H2,1-3H3,(H,25,29)(H,26,27)/t15-/m1/s1
InChI Key
XXXSUGLINJXRGT-OAHLLOKOSA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1. Catalytic ozonation of 2, 2'-methylenebis (4-methyl-6-tert-butylphenol) over nano-Fe3O4@cow dung ash composites: Optimization, toxicity, and degradation mechanisms
Cui Ma, Shengyong Jia, Pengfei Yuan, Zhengguang He Environ Pollut. 2020 Oct;265(Pt B):114597. doi: 10.1016/j.envpol.2020.114597. Epub 2020 Apr 22.
Composite magnetic oxide at cow dung ash, nano-Fe3O4@cow dung ash (nano-Fe3O4@CDA), was used as catalytic material for the degradation of 2, 2'-methylenebis (4-methyl-6-tert-butylphenol) (AO 2246) in real biologically pretreated landfill leachate. The Fe3O4@CDA composite exhibited catalytic ozonation activity and allowed material separation and magnetic recovery. The effects of several operating parameters including O3 concentration, catalyst dosage, temperature and scavengers were evaluated in parallel. Over 70% of AO 2246 were removed by the nano-Fe3O4@CDA/O3 system under optimum conditions within 120min reaction time. The EPR, GC-MS and free-radical quenching experiments expatiated the mechanism of this degradation process. It was confirmed that the AO 2246 was degraded efficiently in this catalytic micro-ozonation process, Additionally, GC-MS analysis state clearly that the 3,5-bis(1,1-dimethylethyl)phenol, 4-(1,5-dihydroxy-2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-one, ethanone, 1-(1,4-dimethyl-3-cyclohexen-1-yl)-, 5-tert-butyl-6-3, 5-diene-2-one, 2-hydroxyhexanoic acid, 2-propenoic acid 1,1-dimethylethyl ester, butanoic acid, 2-methyl-, methyl ester and propanoic acid, 2, 2-dimethyl- were the dominant oxidation products (OPs) during the degradation of the AO 2246. The EPR results showed that the catalytic ozonation over Fe3O4@CDA led to produce more hydroxyl radicals, which were in favor of AO 2246 degradation. The toxicity evolution was also performed through a QSAR analysis calculated by the ECOSAR program which further demonstrated the different responses toward the AO 2246 and its OPs.
2. Octyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate: complex sheets built from N-H···N, C-H···N and C-H···O hydrogen bonds
Edwar Cortés, Rodrigo Abonía, Justo Cobo, Christopher Glidewell Acta Crystallogr C Struct Chem. 2014 Jun;70(Pt 6):617-21. doi: 10.1107/S2053229614011760. Epub 2014 May 24.
In the title compound, C29H35ClN4O2, the bond lengths provide evidence for aromatic delocalization in the pyrazole ring but bond fixation in the fused imidazole ring, and the octyl chain is folded, rather than adopting an all-trans chain-extended conformation. A combination of N-H···N, C-H···N and C-H···O hydrogen bonds links the molecules into sheets, in which the hydrogen bonds occupy the central layer with the tert-butyl and octyl groups arranged on either side, such that the closest contacts between adjacent sheets involve only the octyl groups. Comparisons are made with the supramolecular assembly in some simpler analogues.
3. Estrogenic activity of benzotriazole UV stabilizers evaluated through in vitro assays and computational studies
Hongru Feng, Huiming Cao, Juan Li, Haiyan Zhang, Qiao Xue, Xian Liu, Aiqian Zhang, Jianjie Fu Sci Total Environ. 2020 Jul 20;727:138549. doi: 10.1016/j.scitotenv.2020.138549. Epub 2020 Apr 13.
Benzotriazole UV stabilizers (BUVs) are used in a variety of products to prevent yellowing and degradation. However, knowledge of the estrogenic activity of BUVs is still lacking. In the present study, a strategy combining in vitro assays and computational studies was adopted to evaluate the estrogenic activity of BUVs. 2-(2-Hydroxy-5-methlphenyl) benzotriazole (UV-P), 2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole (UV-PS), and 2-(3-Allyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole (UV-9) induced partial estrogenic activity while 2-(2-hydroxy-5-tert-octyl-phenyl)benzotriazole (UV-329), 2-(3-s-butyl-5-tert-butyl-2-hydroxyphenyl)benzotriazole (UV-350), and 3-(2H-benzotriazolyl)-5- (1,1-di-methylethyl)-4-hydroxy-benzene-propanoic acid octyl esters (UV-384) showed no estrogenic activity in MVLN assays. The results of in vitro assays were in accord with the results of computational studies. Moreover, ICI 182,780 suppressed the estrogenic activity of BUVs both in the absence and presence of E2, demonstrating that the estrogen responsive element (ERE) transcription activities of BUVs are generated through an estrogen receptor (ER) mediated pathway. Our findings suggest that the endocrine disruption effects of BUVs are a cause for concern.
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