scholarly journals Cholesterol’s Aliphatic Side Chain Modulates Membrane Properties

2013 ◽  
Vol 52 (49) ◽  
pp. 12848-12851 ◽  
Author(s):  
Holger A. Scheidt ◽  
Thomas Meyer ◽  
Jörg Nikolaus ◽  
Dong Jae Baek ◽  
Ivan Haralampiev ◽  
...  
Keyword(s):  
Membrane Properties ◽  
Side Chain ◽  
Aliphatic Side Chain

scholarly journals Cholesterol's Aliphatic Side Chain Structure Modulates Membrane Properties

2016 ◽  
Vol 110 (3) ◽  
pp. 84a
Author(s):  
Daniel Huster ◽  
Thomas Meyer ◽  
Jörg Nikolaus ◽  
Dong Jae Baek ◽  
Ivan Haralampiev ◽  
...  
Keyword(s):  
Chain Structure ◽  
Membrane Properties ◽  
Side Chain ◽  
Aliphatic Side Chain

Influence of the sterol aliphatic side chain on membrane properties: a molecular dynamics study

2015 ◽  
Vol 17 (35) ◽  
pp. 22736-22748 ◽  
Author(s):  
João R. Robalo ◽  
J. P. Prates Ramalho ◽  
Daniel Huster ◽  
Luís M. S. Loura
Keyword(s):  
Molecular Dynamics ◽  
Membrane Properties ◽  
Side Chain ◽  
Side Chains ◽  
Aliphatic Side Chain ◽  
Acyl Chains ◽  
Hydrophobic Matching ◽  
Phospholipid Acyl Chains

Cholesterol provides best hydrophobic matching, induces maximal membrane ordering, and displays highest preference for saturated phospholipid acyl chains, among a homologous ser ies of sterols with side chains of varying lengths.

scholarly journals Membrane properties of cholesterol analogs with an unbranched aliphatic side chain

2014 ◽  
Vol 184 ◽  
pp. 1-6 ◽  
Author(s):  
Thomas Meyer ◽  
Dong Jae Baek ◽  
Robert Bittman ◽  
Ivan Haralampiev ◽  
Peter Müller ◽  
...  
Keyword(s):  
Membrane Properties ◽  
Side Chain ◽  
Aliphatic Side Chain

Peptide folding induced by Cα-methylated, chiral α-acids with a long aliphatic side chain

2006 ◽  
pp. 270-271
Author(s):  
Marco Crisma ◽  
Cristina Peggion ◽  
Fernando Formaggio ◽  
Bernard Kaptein ◽  
Quirinus B. Broxterman ◽  
...  
Keyword(s):  
Peptide Folding ◽  
Side Chain ◽  
Aliphatic Side Chain

scholarly journals Efficient Synthesis of α-Branched Purine-Based Acyclic Nucleosides: Scopes and Limitations of the Method

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4307
Author(s):  
Jan Frydrych ◽  
Lenka Poštová Slavětínská ◽  
Martin Dračínský ◽  
Zlatko Janeba
Keyword(s):  
Acetic Anhydride ◽  
Room Temperature ◽  
Side Chain ◽  
Efficient Synthesis ◽  
Purine Derivatives ◽  
Aliphatic Side Chain ◽  
Acyclic Nucleosides ◽  
Efficient Route ◽  
High Yields ◽  
Trimethylsilyl Trifluoromethanesulfonate

An efficient route to acylated acyclic nucleosides containing a branched hemiaminal ether moiety is reported via three-component alkylation of N-heterocycle (purine nucleobase) with acetal (cyclic or acyclic, variously branched) and anhydride (preferentially acetic anhydride). The procedure employs cheap and easily available acetals, acetic anhydride, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). The multi-component reaction is carried out in acetonitrile at room temperature for 15 min and provides moderate to high yields (up to 88%) of diverse acyclonucleosides branched at the aliphatic side chain. The procedure exhibits a broad substrate scope of N-heterocycles and acetals, and, in the case of purine derivatives, also excellent regioselectivity, giving almost exclusively N-9 isomers.

An α-diketone from the condensation product of glucose and ethyl acetoacetate

1964 ◽  
Vol 17 (10) ◽  
pp. 1174 ◽  
Author(s):  
LK Dalton
Keyword(s):  
Hydrogen Peroxide ◽  
Solid State ◽  
Hydrogen Chloride ◽  
Ethyl Acetoacetate ◽  
Condensation Product ◽  
Side Chain ◽  
Furoic Acid ◽  
Aliphatic Side Chain ◽  
Benzilic Acid ◽  
Reversible Cyclization

When the product from the condensation of glucose and ethyl acetoacetate, ethyl 2-D-arabino-tetrahydroxybutyl-5-methyl-4-furoate (Ia), is heated in ethanolic hydrogen chloride, an a-diketone (IVa) is produced. It exists as a mono-enol in solution and in the solid state. Although this diketone is formed with an aliphatic side chain, there is at first a predominant, but reversible, cyclization to the "difuran" (II). With hydrogen peroxide the diketone yields 2-carboxymethy1-5- methyl-4-furoic acid (VII), and with alkali it undergoes a benzilic acid rearrangement.

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