N-α-(t-Butoxycarbonyl)-L-homoserine benzyl ester
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N-α-(t-Butoxycarbonyl)-L-homoserine benzyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-003130
CAS number
105183-60-6
Molecular Formula
C16H23NO5
Molecular Weight
309.36
N-α-(t-Butoxycarbonyl)-L-homoserine benzyl ester
Synonyms
Boc-Hse-OBzl; Boc-homoSer-OBzl; (2S)-2-tert-butoxycarbonylamino-4-hydroxybutyric acid benzyl ester
Purity
≥ 95%
Density
1.154±0.060 g/cm3
Melting Point
58-59 °C
Boiling Point
467.4±45.0 °C
InChI
InChI=1S/C16H23NO5/c1-16(2,3)22-15(20)17-13(9-10-18)14(19)21-11-12-7-5-4-6-8-12/h4-8,13,18H,9-11H2,1-3H3,(H,17,20)/t13-/m0/s1
InChI Key
YQTGYJUMDNISEP-ZDUSSCGKSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCO)C(=O)OCC1=CC=CC=C1
1.Structure-activity relationship studies of new rifamycins containing l-amino acid esters as inhibitors of bacterial RNA polymerases.
Czerwonka D1, Domagalska J1, Pyta K1, Kubicka MM2, Pecyna P2, Gajecka M3, Przybylski P4. Eur J Med Chem. 2016 Mar 24;116:216-221. doi: 10.1016/j.ejmech.2016.03.061. [Epub ahead of print]
New rifamycins (1-12) combined with different l-amino acids, containing methyl, ethyl, tert-butyl and benzyl groups at the ester part, via amine linkage, were synthesized and their structures in solution were determined by spectroscopic FT-IR and 1D and 2D NMR methods as well as visualized by DFT calculations. Two types of rifamycin structures were detected in solution: a zwitterionic one with the transferred proton from O(8)H phenol to secondary N(38) atom and a pseudocyclic structure stabilized via formation of intramolecular H-bond within the protonated basic C(3)-substituent. The presence of these rifamycins' structures influenced physico-chemical (logP, solubility) parameters and antibacterial properties. The bulkiness at the ester substituent of new rifamycins containing aromatic l-amino acids was found to be an important factor, besides the solubility, to achieve relatively high antibacterial activity against reference S. epidermidis and reference S.
2.CuH-Catalysed Hydroamination of Styrene with Hydroxylamine Esters: A Coupled Cluster Scrutiny of Mechanistic Pathways.
Tobisch S1. Chemistry. 2016 May 3. doi: 10.1002/chem.201600230. [Epub ahead of print]
A detailed computational exploration of mechanistic intricacies of the copper(I) hydride (CuH)-catalysed hydroamination of styrene with a prototype hydroxylamine ester by a recently reported [(dppbz)CuH] catalyst (dppbz≡{P^P}≡1,2-bis(diphenylphosphino)-benzene) is presented. A variety of plausible mechanistic avenues have been pursued by means of a sophisticated computational methodology, from which a general understanding of the factors controlling hydroamination catalysis emerged. The catalytically competent {P^P}CuI hydride, which is predominantly present as its dimer, involves in irreversible hydrocupration proceeding with complete 2,1 regioselectivity to form a secondary {P^P}CuI benzyl intermediate. Its interception with benzylamine ester produces the branched tertiary amine product and {P^P}CuI benzoate upon intramolecular SN 2 disruption of the amine electrophile's N-O linkage, to precede a highly rapid, strongly exergonic C-N bond-forming reductive elimination.
3.Inhibitory mechanism of phthalate esters on Karenia brevis.
Liu N1, Wen F2, Li F3, Zheng X4, Liang Z1, Zheng H5. Chemosphere. 2016 May 2;155:498-508. doi: 10.1016/j.chemosphere.2016.04.082. [Epub ahead of print]
The occurrence of phthalate esters (PAEs), a class of widely used and environmentally prevalent chemicals, raises concern to environmental and human health globally. The PAEs have been demonstrated to inhibit algae growth, but the underlying mechanisms remain unclear. In this research, diethyl ortho-phthalate (DEP), diallyl phthalate (DAP), di-n-butyl ortho-phthalate (DBP), di-iso-butyl ortho-phthalate, and benzyl-n-butyl ortho-phthalate (BBP) were screened from 11 species of PAEs to study their inhibitory effects on Karenia brevis and determine their target sites on algae. With increasing the alkyl chains of these five PAEs, the values of EC50,96h decreased. The content of malondialdehyde increased with the continuous accumulation of reactive oxygen species (ROS) in the algae cells. Moreover, the superoxide dismutase and catalase contents were first activated and then inhibited. The ultrastructures of Karenia brevis cells were detected by transmission electron microscopy, and cells treated with PAEs exhibiting distorted shapes and large vacuoles.
4.Using water plug-assisted analyte focusing by micelle collapse in combination with microemulsion electrokinetic chromatography for analyzing phthalate esters.
Chao HC1, Liao HW1, Kuo CH2. J Chromatogr A. 2016 May 6;1445:149-57. doi: 10.1016/j.chroma.2016.03.086. Epub 2016 Apr 1.
Phthalate plasticizers are widely used in the plastics industry, but they have been detected in soft drinks, pharmaceuticals and food products. This study developed a method that uses water plug-assisted analyte focusing by micelle collapse and microemulsion electrokinetic chromatography (WPA-AFMC-MEEKC) for quantifying benzyl butyl phthalate (BBP), dibutyl phthalate (DBP), diethylhexyl phthalate (DEHP), and diisodecyl phthalate (DIDP) in pediatric pharmaceuticals. The AFMC strategy was applied to improve the detection sensitivity, and a short water plug was introduced to assist micelle collapse in the micelle dilution zone for sample stacking. To carry neutral phthalates into the capillary through electrokinetic injection, sodium dodecyl sulfate (SDS) was added to the sample solution, and 8mM SDS was selected as the optimal concentration. The optimized background solution (BGS) contained 16.13mM phosphate buffer (pH=2.5), 150mM SDS, 0.75% n-octane (v/v), 5% 1-butanol (BuOH), 22.
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