Browse
Submit Data
Databases
API
Help

Dataset Information

17 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

On the Preparation of Enantiomerically Pure Isonitriles from Amino Acid Esters and Peptides.

ABSTRACT: An improved method for the synthesis of enantiomerically pure isonitriles from amino acid esters and dipeptides is described.

SUBMITTER: Zhu J

PROVIDER: S-EPMC3159893 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

On the Preparation of Enantiomerically Pure Isonitriles from Amino Acid Esters and Peptides.

Zhu Jianglong J Wu Xiangyang X Danishefsky Samuel J SJ

Tetrahedron letters 20090201 5

An improved method for the synthesis of enantiomerically pure isonitriles from amino acid esters and dipeptides is described. ...[more]

PMID: 21869850

Similar Datasets

Synthesis and antioxidant evaluation of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters from modified ?-amino acids.

Project description:The efforts for synthesis of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters 6 are reported in good yields from an in situ generated ?-azidomethyl ketone. Optimum experimental conditions were established for preparation of ?-halomethyl ketones 10 and ?-N,N-dipropargylamino esters 11, all derived from ?-amino acids. The starting materials reacted under conventional click chemistry conditions, revealing a specific reactivity of bromomethyl ketones over chloromethyl ketones. The antioxidant activity of compounds 6 was assayed by DPPH method. The compound 6c with an IC50 of 75.57 ± 1.74 ?g mL(-1) was the most active. Technically, this methodology allows the preparation of a combinatorial library of analogues with different structural characteristics depending on the nature of the modified ?-amino acids employed in the synthesis.

| S-EPMC4216715 | biostudies-literature

Preparation and reactions of N-thioformyl peptides from amino thioacids and isonitriles.

Project description:The preparation of N-thioformyl peptides from amino thioacids and isonitriles at room temperature is described.

| S-EPMC2690959 | biostudies-literature

Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of ?-Amino Acids.

Project description:A high yielding and practical two-step synthesis of enantiomerically pure perfluorobutanesulfinamide from Senanayake's 2-aminoindanol-derived sulfinyl transfer reagent was developed and carried out on a multigram scale. Straightforward condensation of this sulfinamide with ethyl glyoxylate provided the N-perfluorobutanesulfinyl imino ester. The utility of this activated N-sulfinyl imino ester was demonstrated for reactions that gave either no product or very low yields with the corresponding less electrophilic N-tert-butanesulfinyl derivative. Specifically, the Rh(III)-catalyzed C-H bond addition of aromatic compounds to the N-perfluorobutanesulfinyl imino ester provided arylglycines with very high diastereoselectivities for a range of directing groups including pyrrolidine amide, azo, sulfoximine, 1-pyrazole, and 1,2,3-triazole functionalities. Thermal asymmetric aza-Diels-Alder reactions also proceeded in good yields and with high selectivity, including for the substituted dienes (E)-1,3-pentadiene and (2E,4E)-2,4-hexadiene.

| S-EPMC4761297 | biostudies-literature

Enantiomerically pure alpha-amino aldehydes from silylated alpha-amino acids.

Project description:The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that < or =2% racemization occurs in the 1 --> 8 conversions.

| S-EPMC2563420 | biostudies-literature

One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected ?-amino esters.

Project description:An improved protocol for the synthesis of enantiomerically pure allylic amines is reported. N-Protected ?-amino esters derived from natural amino acids were submitted to a one-pot tandem reduction-olefination process. The sequential reduction with DIBAL-H at -78 °C and subsequent in situ addition of organophosphorus reagents yielded the corresponding allylic amines without the need to isolate the intermediate aldehyde. This circumvents the problem of instability of the aldehydes. The method tolerates well both Wittig and Horner-Wadsworth-Emmons organophosphorus reagents. A better Z-(dia)stereoselectivity was observed when compared to the previous one-pot method. The (dia)stereoselectivity of the process was affected neither by the reaction solvent nor by the amount of DIBAL-H employed. The method is compatible with the presence of free hydroxy groups as shown with serine and threonine derivatives.

| S-EPMC4902051 | biostudies-other

Structural characterization of an enantiomerically pure amino acid imidazolide and direct formation of the beta-lactam nucleus from an alpha-amino acid.

Project description:Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected 3-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired 3-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.

| S-EPMC2597468 | biostudies-literature

Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Aminoalkyl)boronic Esters.

Project description:AbstractCyclic sulfamidates undergo borylation under copper‐catalyzed conditions using Bpin to give enantiomerically (and diasteromerically) defined (aminoalkyl)boronic esters. External iodide is essential, but the intermediacy of simple alkyl iodides has been excluded; ‐sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon‐centered radicals under these copper‐catalyzed conditions appears likely.

| S-EPMC4770434 | biostudies-other

Enantiomerically Pure Tetravalent Neptunium Amidinates: Synthesis and Characterization.

Project description:The synthesis of a tetravalent neptunium amidinate [NpCl((S)-PEBA)3 ] (1) ((S)-PEBA=(S,S)-N,N'-bis-(1-phenylethyl)-benzamidinate) is reported. This complex represents the first structurally characterized enantiopure transuranic compound. Reactivity studies with halide/pseudohalides yielding [NpX((S)-PEBA)3 ] (X=F (2), Br (3), N3 (4)) have shown that the chirality-at-metal is preserved for all compounds in the solid state. Furthermore, they represent an unprecedented example of a structurally characterized metal-organic Np complex featuring a Np-Br (3) bond. In addition, 4 is the only reported tetravalent transuranic azide. All compounds were additionally characterized in solution using para-magnetic NMR spectroscopy showing an expected C3 -symmetry at low temperatures.

| S-EPMC7497184 | biostudies-literature

Enantiomerically pure trans-beta-lactams from alpha-amino acids via compact fluorescent light (CFL) continuous-flow photolysis.

Project description:Photolysis of alpha-diazo-N-methoxy-N-methyl (Weinreb) beta-ketoamides derived from enantiomerically pure (EP) alpha-amino acids affords the corresponding EP beta-lactams via an intramolecular Wolff rearrangement. The photochemistry is promoted with either standard UV irradiation or through the use of a 100 W compact fluorescent light; the latter affords a safe and environmentally friendly alternative to standard photolysis conditions. A continuous-flow photochemical reactor made from inexpensive laboratory equipment reduced reaction times and was amenable to scale-up. The diastereoselectivity (cis or trans) of the product beta-lactams has been shown to vary from modest to nearly complete. An extremely facile, atom-economical method for the epimerization of the product mixture to the trans isomer, which is generally highly crystalline, has been developed. Evidence for C3 epimerization of Weinreb amide structures via a nonbasic, purely thermal route is presented. Subsequent transformations of both the Weinreb amide at C3 (beta-lactam numbering) and the amino acid side chain at C4 are well-tolerated, allowing for a versatile approach to diverse beta-lactam structures. The technology is showcased in the synthesis of a common intermediate used toward several carbapenem-derived structures starting from unfunctionalized aspartic acid.

| S-EPMC2924779 | biostudies-literature

Chemoenzymatic dynamic kinetic resolution: a powerful tool for the preparation of enantiomerically pure alcohols and amines.

Project description:Chemoenzymatic dynamic kinetic resolution (DKR) constitutes a convenient and efficient method to access enantiomerically pure alcohol and amine derivatives. This Perspective highlights the work carried out within this field during the past two decades and pinpoints important avenues for future research. First, the Perspective will summarize the more developed area of alcohol DKR, by delineating the way from the earliest proof-of-concept protocols to the current state-of-the-art systems that allows for the highly efficient and selective preparation of a wide range of enantiomerically pure alcohol derivatives. Thereafter, the Perspective will focus on the more challenging DKR of amines, by presenting the currently available homogeneous and heterogeneous methods and their respective limitations. In these two parts, significant attention will be dedicated to the design of efficient racemization methods as an important means of developing milder DKR protocols. In the final part of the Perspective, a brief overview of the research that has been devoted toward improving enzymes as biocatalysts is presented.

| S-EPMC4415027 | biostudies-other

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data