Dipeptide Isosteres Research Articles

Palladium(0)-Catalyzed Isomerization Reactions of Aziridines Bearing an alpha,beta-Unsaturated Ester Group: A Thermodynamic Preference for Chiral Alkyl (2E)-4,5-cis-4,5-Epimino-N-(alkyl- or arylsulfonyl) 2-Enoates over the Other Three Stereoisomers.

Palladium(0)-catalyzed reactions of five sets of four stereoisomeric 4,5-epimino-N-(methanesulfonyl) or -N-(arylsulfonyl) 2-enoates reveal that 4,5-cis-(2E)-isomers are thermodynamically more stable than other isomers, in accord with calculations. A highly stereoselective synthesis of (E)-alkene dipeptide isosteres having the desired stereochemistries from unwanted stereoisomeric 4,5-epimino-N-(arylsulfonyl) 2-enoates is also presented.

A simple, stereoselective synthesis of ketomethylene dipeptide isosteres

Abstract An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-γ-ketoesters) from Cbz-protected amino acids and scalemic 2-triflyloxy esters has been developed. The method is short (three steps), efficient, and highly diastereoselective and enantioselective.

Zinc-Mediated Allylation of N-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of Phe-Phe Hydroxyethylene Dipeptide Isosteres

An efficient route for the synthesis of a Phe-Phe hydroxyethylene dipeptide isostere utilized for the design of potential inhibitors of renin and HIV-protease was developed.

Highly Diastereoselective, Nucleophilic Alkenoylation of Enantiopure α-Oxy- and α-Aminoalkanals by Lithiated [1-(p-Toluenesulfonyl)alk-2-enyl] Carbamates. Revision of the Stereochemistry and Application to the Synthesis of a Dihydroxyethylene Dipeptide Isostere

Highly Diastereoselective, Nucleophilic Alkenoylation of Enantiopure α-Oxy- and α-Aminoalkanals by Lithiated [1-(p-Toluenesulfonyl)alk-2-enyl] Carbamates. Revision of the Stereochemistry and Application to the Synthesis of a Dihydroxyethylene Dipeptide Isostere

Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method

Recent advances in the syntheses of enantiopure synthetic building blocks useful for non-protein amino acids, dipeptides, oligopeptides using solid state peptide synthesis, isoserines (norstatines), dipeptide isosteres [hydroxy(keto)ethylene, hydroxyethylamine, hydroxyethylene and dihydroxyethylene isosteres], taxoids, polyamines, poly(amino alcohol)s and poly(amino ether)s, and other biologically active compounds through applications of the β-lactam Synthon method is reviewed.

Regiospecific ring-opening reactions of aziridines bearing an α,β-unsaturated ester group with trifluoroacetic acid or methanesulfonic acid: application to the stereoselective synthesis of (E)-alkene dipeptide isosteres

Reaction of N-(2,4,6-trimethylphenylsulfonyl)-γ,δ-cis- or -trans-γ,δ-epimino (E)-α,β-enoates with acids such as TFA or methanesulfonic acid (MSA) affords the stereo- and regio-selective ring-opened products in high yields, and subsequent treatment of resulting δ-aminated γ-mesyloxyα,β-enoates with organocopper reagents yields diastereoisomerically pure (E)-alkene dipeptide isosteres.

A Highly Stereoselective Synthesis of the Functionalized (E)-Alkene Dipeptide Isostere of Trp-Val via Organocyanocopper-Lewis Acid Mediated Reaction.

A stereocontrolled synthesis of the (E)-alkene dipeptide isostere of Trp-Val is described. The stereospecific α-alkylation of the δ-amino-γ-mesyloxy-α, β-unsaturated ester via the organocyanocopper-Lewis acid mediated reaction, based on 1, 3-transfer of chirality, was successfully applied for the key step in the synthetic sequence.

ChemInform Abstract: A New Chiral, Cationic β‐Amino Alcohol Equivalent: A Variable Approach to Enantiomerically Pure Building Blocks for Hydroxyethylene Dipeptide Isosteres.

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: Bioactive Hydroxyethylene Dipeptide Isosteres with Hydrophobic (P3‐P1)‐ Moieties. A Novel Strategy Towards Small Non‐Peptide Renin Inhibitors.

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: Excellent Chiral Introduction by Diene Iron‐Tricarbonyl Moiety. Part 3. Asymmetric Synthesis of Hydroxyethylidene Dipeptide Isostere Using a Diastereoselective 1,2‐Nucleophilic Addition of Organocerium Reagents into a 1‐Azatriene Fe(CO)3 Complex.

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: Synthesis and Derivatization of a Versatile α‐Substituted Lactam Dipeptide Isostere.

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: Asymmetric Synthesis of the Abbott Amino Dihydroxyethylene Dipeptide Isostere Subunit.

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: Stereoselective Synthesis of Hydroxyethylene Dipeptide Isostere from Sugar.

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: A Practical and Diastereoselective Synthesis of Ketomethylene Dipeptide Isosteres of the Type AAψ(COCH2)Asp.

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.

Bioactive hydroxyethylene dipeptide isosteres with hydrophobic (P 3-P 1)-moieties. A novel strategy towards small non-peptide renin inhibitors

The design and synthesis of new truncated δ-amino hydroxyethylene dipeptide isosteres lacking the P 4-P 2 peptide backbone is described. The most active compounds 15c and 30c inhibited human renin in the submicromolar range. This promising concept may offer the possibility to discover completely non-peptide, lowmolecular weight renin inhibitors with improved pharmacokinetic properties.

ChemInform Abstract: Ritter Reaction of Cyclic Hydroxyamines: Synthesis of Conformationally‐ Restricted Reduced Amide Dipeptide Isosteres.

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.

Asymmetric synthesis of the Abbott amino dihydroxyethylene dipeptide isostere subunit

The aminodiol 1b, a N-benzyl protected form of the Abbou dipeptide isostere 1a is prepared, starting from an appropriate α,β-unsaturated ester, involving an asymmetric dihydroxylation and a rearrangement of an intermediate anti α,β-aminoepoxide.

Synthesis and derivatization of a versatile α-substituted lactam dipeptide isostere

The diastereoselective synthesis of a versatile lactam constrained dipeptide isostere is described. The facile derivatization of this intermediate is demonstrated.

Stereoselective Synthesis of Hydroxyethylene Dipeptide Isostere from Sugar

Abstract Regioselective opening of the aziridine ring in the carbohydrate-based precursor led to the stereoselective synthesis of N-Boc-O-benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid methyl ester, the hydroxyethylene dipeptide isostere moiety of potent HIV-1 protease inhibitor.

ChemInform Abstract: Thiazole‐Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV‐1 Aspartic Protease.

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.