Synthesis of Indole-Derived Fluorine-Containing Amino Acids

نویسندگان

  • Hannah C. Cade
  • Mark Blocker
  • Abid Shaikh
چکیده

A Brønsted acid promoted direct aminoalkylation of various indoles with trifluoromethyl oxazolidine is described. A catalytic amount of triflic acid provided straightforward access to the corresponding trifluoromethyled amino esters under mild reaction conditions and a short reaction time of 4 h. On further hydrogenolysis and hydrolysis of ester, the synthesis of indole derived unnatural trifluoromethylated amino acids was achieved. Journal of Nature and Science, 1(8):e169, 2015

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Fluorine containing amino acids: synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif.

A synthesis of two (S)-phenylalanine derivatives is described which have the all-cis, 2,3,5,6-tetrafluorocyclohexyl motif attached to the aromatic ring at the meta and para positions; the para substituted isomer is elaborated into illustrative dipeptides via the free amine and carboxylate respectively demonstrating its utility as a novel amino acid for peptide synthesis and offering a vehicle f...

متن کامل

Pharmacological properties of some 3-substituted indole derivatives, a concise overview

Indole is a nitrogen-containing heterocycle. It is a very important motif in agriculture and pharmacy. Many compounds containing indole moiety has been isolated form nature. It is also an important part in natural alkaloids. Tryptophan is an amino acid which posses indole. 3-Sustituted indoles are the main group of its derivatives. Because the wide-spread application of 3-substituted indolic co...

متن کامل

Fluorine: a new element in protein design.

Fluorocarbons are quintessentially man-made molecules, fluorine being all but absent from biology. Perfluorinated molecules exhibit novel physicochemical properties that include extreme chemical inertness, thermal stability, and an unusual propensity for phase segregation. The question we and others have sought to answer is to what extent can these properties be engineered into proteins? Here, ...

متن کامل

The Acid Strength of the Amino Group as a Factor in the Transport of Amino Acids.

I. Halogen atoms have been introduced on the Ê-carbons of amino acids in order to dissociate effects on pKa of the amino group on transport, from effects of the hydrophilic or hydrophobic character of the side chain. 2. ~-Monofluoromethyland a-trifluoromethylalanine have been synthesized by adaptations of the Strecker synthesis. The pKa of the amino group in these 2 cases was lowered by x.6 and...

متن کامل

Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

A new series of spiropyrrolidine compounds containing indole/indazole moieties as side chains have been accomplished via a one-pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions ...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2015