Synthesis Of Dehydroamino Acids Research Articles

Stereoselective Synthesis of Dehydroamino Acids and Its Application to the Synthesis of Nitrogen-containing Natural Products

Stereoselective Synthesis of Dehydroamino Acids and Its Application to the Synthesis of Nitrogen-containing Natural Products

Synthesis of Dehydroamino Acids through Stereospecific Elimination

Key words dehydroamino acids - asymmetric synthesis - cyclic sulfamidites - phomopsin - hydroxyamino acids - elimination

ChemInform Abstract: The Synthesis of Dehydrotryptophan and Dehydrotryptophan‐Containing Peptides.

AbstractReview: 95 refs.

The synthesis of dehydrotryptophan and dehydrotryptophan-containing peptides

Dehydrotryptophan and its derivatives are non-proteinogenic amino acids commonly found in peptide-based natural products produced by microorganisms, marine organisms and plants. These non-proteinogenic amino acids are found in secondary metabolites and are formed by post translational modification processes. Although comprehensive reviews on the synthesis of dehydroamino acids are available, this perspective focuses solely on methods to synthesise the dehydrotryptophan-containing segment of naturally occurring peptides, amino acids and their derivatives.

Divergent routes to chiral cyclobutane synthons from (-)-alpha-pinene and their use in the stereoselective synthesis of dehydro amino acids.

Several polyfunctionalized cyclobutane derivatives have been synthesized using commercial (-)-alpha-pinene and (-)-verbenone as chiral precursors. Thus, oxidative cleavage of these compounds by using ruthenium trichloride afforded quantitatively (-)-cis-pinonic and (-)-cis-pinononic acids, respectively, without epimerization. These products were converted into several types of aldehydes, which are the key intermediates in the synthesis of cyclobutane dehydro amino acids via Wittig-Horner condensations with suitable phosphonates. These reactions are highly stereoselective, affording exclusively (Z) isomers, stereochemistry being assessed by NMR experiments. The obtained dehydro amino acids are polyfunctionalized molecules useful for the synthesis of other alpha-amino acids, with additional chiral centers, whose configuration must be induced by the chirality of the terpene employed as a precursor.

ChemInform Abstract: The Synthesis of Dehydroamino Acids from Pyruvic Acid.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Nucleophilic α‐Addition to Alkynoates. A Synthesis of Dehydroamino Acids.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The Synthesis of Dehydroamino Acids from Pyruvic Acid

Dehydroamino acids can be prepared in a one-pot reaction from pyruvates in 47-74% yield.

Nucleophilic α-Addition to Alkynoates. A Synthesis of Dehydroamino Acids

Nucleophilic α-Addition to Alkynoates. A Synthesis of Dehydroamino Acids

Synthesis of dehydroamino acids and didehydrodioxopiperazines and their conversion into α‐mercapto‐α‐amino acid derivatives

AbstractA synthesis of α,β‐dehydroamino acid derivatives 12 is described, which is of possible general applicability and might be useful for the preparation of peptides which have such a moiety in their sequence. In addition, several didehydrodioxopiperazines (13–17) have been prepared. The reactivity of these compounds towards liquid H2S in the presence of ZnCl2 has been studied. Only the dehydroalanine derivatives 12a and 13 gave α‐addition products; all other dehydroamino acid derivatives and cyclic dipeptides failed to react cleanly.

Synthesis of dehydro amino acids and peptides by dehydrosulfenylation. Rate enhancement using sulfenic acid trapping agents.

Synthesis of dehydro amino acids and peptides by dehydrosulfenylation. Rate enhancement using sulfenic acid trapping agents.