Synthesis of N‐Protected α‐Amino Acids from N‐(Benzyloxycarbonyl)‐L‐Serine via its β‐Lactone: Nα‐(Benzyloxycarbonyl)‐β‐(Pyrazol‐1‐yl)‐L‐Alanine

doi:10.1002/0471264180.OS070.01

Paper

Synthesis of N‐Protected α‐Amino Acids from N‐(Benzyloxycarbonyl)‐L‐Serine via its β‐Lactone: Nα‐(Benzyloxycarbonyl)‐β‐(Pyrazol‐1‐yl)‐L‐Alanine

Published Apr 28, 2003 · S. Pansare, G. Huyer, L. Arnold

Organic Syntheses

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Abstract

Synthesis of N-protected α-amino acids from N-(benzyloxycarbonyl)-l-serine via its β-lactone: Nα-(benzyloxycarbonyl)-β-(pyrazol-1-yl)-l-alanine intermediate: N-(benzyloxycarbonyl)-L-serine β-lactone product: Nα-(benzyloxycarbonyl)-β-(pyrazol-1-yl)-L-alanine product: pyrazolylalanine Keywords: alkylation, N-alkylation; alkylation, O-alkylation; annulation, heterocyclic-[4]; cyclization, condensation; ring opening reactions; acetonitrile; tetrahydrofuran; diethyl azodicarboxylate, explosion hazard; dimethyl azodicarboxylate, explosion hazard

Study Snapshot

N-protected -amino acids can be synthesized from N-(benzyloxycarbonyl)-l-serine via its -lactone, yielding pyrazolylalanine.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of N‐Protected α‐Amino Acids from N‐(Benzyloxycarbonyl)‐L‐Serine via its β‐Lactone: Nα‐(Benzyloxycarbonyl)‐β‐(Pyrazol‐1‐yl)‐L‐Alanine

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References

Biomimetic Synthesis of Heterocyclic β-Substitutd Alanines by Pyridoxal 5'-Phosphate-Catalyzed Chemical Reactions

Pyridoxal 5'-phosphate-catalyzed chemical reactions can efficiently synthesize heterocyclic -substituted alanines, with metal ions and pH playing crucial roles in the process.

Mechanism of formation of serine β-lactones by Mitsunobu cyclization: synthesis and use of L-serine stereospecifically labelled with deuterium at C-3

Mitsunobu cyclization of L-serine leads to formation of serine -lactones through hydroxy group activation, with inversion of configuration at C-3 and retention of carboxy oxygens.

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This study demonstrates that potassium ferricyanide can effectively convert 1,2-dicarboxylate groups to double bonds, providing a new method for preparing chiral peptides.

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Asymmetric synthesis of -hydroxy--alkylamino acids can be achieved by asymmetric aldol reaction of -isocyanocarboxylates with chiral ferrocenylphosphine-gold(I) complexes, yielding high

Purification and characterization of β-(pyrazol-1-yl)-l-alanine synthase from Citrullus vulgaris

The enzyme -(pyrazol-1-yl)-l-alanine synthase from Citrullus vulgaris seedlings shows electrophoretic homogeneity and distinct properties from related -substituted alanines and cysteine synthase from other sources.

Citations

New insight into nucleo α-amino acids - Synthesis and SAR studies on cytotoxic activity of β-pyrimidine alanines.

Willardiine and its analogs show antiproliferative activity against cancer cells, with potential for treating brain tumors and glioblastoma.

Synthesis of Nβ-Substituted α,β-Diamino Acids via Stereoselective N-Michael Additions to a Chiral Bicyclic Dehydroalanine.

This method efficiently synthesizes N-substituted,-diamino acids at room temperature, offering a practical approach for synthesis of fluorescent and ciprofloxacin-containing amino acid derivatives.

Predicting Binding to P-Glycoprotein by Flexible Receptor Docking

Flexible receptor docking effectively predicts P-glycoprotein binding specificity, suggesting that specificity in P-gp is better understood by physicochemical properties of ligands and binding sites rather than specific sub-sites.