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Related Concept Videos

SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

10.3K
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
10.3K
SN1 Reaction: Kinetics02:05

SN1 Reaction: Kinetics

9.6K
In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to the SN2 mechanism despite using a strong nucleophile.
However, Sir Christopher Ingold and Edward D. Hughes, who studied the kinetics of various nucleophilic substitution reactions, noticed that a tertiary alkyl halide does undergo a nucleophilic substitution reaction in the presence of a weak nucleophile. While studying the substitution...
9.6K
SN1 Reaction: Mechanism02:25

SN1 Reaction: Mechanism

14.3K
Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow step). The nucleophile is involved only after the slowest step. The SN1 reaction takes place in a multiple-step mechanism. 
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a...
14.3K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

11.2K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
11.2K
Predicting Products: SN1 vs. SN202:27

Predicting Products: SN1 vs. SN2

17.3K
Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the substrate simultaneously as the leaving group departs, in SN1 reactions, the substrate first dissociates to give the carbocation intermediate. Various factors such as the structure of the substrate, the strength of the nucleophile, and the nature of the solvent promote one mechanism over the other.
With increased substitution on the alkyl halide,...
17.3K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.6K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
4.6K

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1-Deoxysphingolipids.

M A Lone1, T Santos2, I Alecu3

  • 1Institute for Clinical Chemistry, University Hospital Zurich, Switzerland; Zurich Center for Integrative Human Physiology (ZIHP), University of Zurich, Switzerland.

Biochimica Et Biophysica Acta. Molecular and Cell Biology of Lipids
|January 10, 2019
PubMed
Summary
This summary is machine-generated.

1-Deoxysphingolipids are unique lipids lacking a key hydroxyl group, preventing their normal metabolism and degradation. Elevated levels of these "headless" sphingolipids are linked to various diseases, highlighting their pathological significance.

Keywords:
AlanineAtypical sphingolipidsGlycineHSAN1SerineSphingolipid metabolismT2DM

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Area of Science:

  • Biochemistry
  • Cell Biology
  • Metabolomics

Background:

  • Sphingolipids (SLs) are essential structural and signaling molecules in eukaryotic cell membranes.
  • 1-Deoxysphingolipids (deoxySLs) are structurally distinct SLs lacking the C1-OH group.
  • This structural difference prevents their conversion into complex SLs and canonical catabolic degradation.

Purpose of the Study:

  • To provide a comprehensive review of 1-deoxysphingolipids.
  • To elucidate the metabolic, physiological, and pathophysiological roles of deoxySLs.
  • To highlight the clinical relevance of aberrant deoxySL accumulation.

Main Methods:

  • Literature review of metabolic pathways.
  • Analysis of physiological functions.
  • Examination of pathophysiological implications in disease states.

Main Results:

  • 1-Deoxysphingolipids cannot be processed through standard SL metabolic or degradation pathways.
  • Pathological accumulation of 1-deoxysphingolipids is associated with several disease conditions.
  • Understanding deoxySL metabolism is crucial for comprehending their disease-associated roles.

Conclusions:

  • 1-Deoxysphingolipids represent a unique class of lipids with distinct metabolic fates.
  • Their aberrant accumulation contributes to disease pathogenesis.
  • Further research into deoxySLs is warranted for potential therapeutic strategies.