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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
(6R,7R)-3-Hydroxymethyl-7-(2-phenyl-acetamido)-3-cephem-4-carboxylic acid lactone
Xiao-Liang Zhou1, Hao Wang, Yan Wang
1Institute of Radiation Medicine, Peking Union Medical College & Chinese Academy of Medical Sciences, Tianjin 300192, People's Republic of China.
Abstract:
In the title compound {systematic name: N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-aza-tricyclo-[6.3.0.0(2,5)]undec-1(8)-en-4-yl]-2-phenyl-acetamide}, C(16)H(14)N(2)O(4)S, the four- and five-membered rings adopt planar conformations (with r.m.s. deviations of 0.0349 and 0.0108 Å respectively) while the six-membered ring adopts a half-chair, or envelope-like, conformation with the S atom in the flap position. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds.
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01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
01:16IUPAC Nomenclature of Carboxylic Acids
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
01:16Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
01:15Carboxylic Acid Derivatives: Overview
01:14Alkylation of β-Diester Enolates: Malonic Ester Synthesis
01:28Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...