tert.-Butyl aminocarbonate (tert.-butyloxycarbonyloxyamine)--a new acylating reagent for amines.

doi:10.1111/J.1399-3011.1984.TB02692.X

Paper

tert.-Butyl aminocarbonate (tert.-butyloxycarbonyloxyamine)--a new acylating reagent for amines.

Published Jan 12, 2009 · R. Harris, I. Wilson

International journal of peptide and protein research

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Abstract

tert.-Butyl amino carbonate (1, tert.-butyloxycarbonyloxyamine) was prepared by reaction of hydroxylamine with di-tert.-butyl dicarbonate (2). 1 was used to acylate different amino acids or amines in water or in aqueous dioxane. 1 was also prepared in situ and used to acylate amino acids directly. 1 reacted 1.5-2.5 times faster than 2 with all amines studied either in water or 50% (v/v) dioxane. Remarkably, 1 retained its ability to acylate amines even in acid solution; the rate of acylation of L-Phe at pH 6.5 (15 M-1 X min-1) was about 20% of the rate at pH 10 (72 M-1 X min-1). 2 was not an acylating reagent below pH 7.0 and as expected, the rate at pH 8.3 (4 M-1 X min-1) was about 10% of that at pH 9.3 (39 M-1 X min-1). Pure BOC-amino acids were obtained in high yield and could be quantitatively deprotected by standard procedures.

Study Snapshot

Tert.-Butyl aminocarbonate is a fast and efficient acylating reagent for amines, with high yield and deprotection potential.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

tert.-Butyl aminocarbonate (tert.-butyloxycarbonyloxyamine)--a new acylating reagent for amines.

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References

Synthesis of tert-butyl aminocarbonate, a new type of compound that can be used to acylate amines

Tert-butyl aminocarbonate rapidly acylates amines in both organic and aqueous solutions, offering a new acylation method.

Glutamic acid is an active site residue of angiotensin I-converting enzyme. Use of the Lossen rearrangement for identification of dicarboxylic acid residues.

The Lossen rearrangement can identify dicarboxylic acid residues in angiotensin I-converting enzyme and carboxypeptidase A, enabling quantitative measurements of diamino acids.

New Method to Prepare N-t-Butoxycarbonyl Derivatives and the Corresponding Sulfur Analogs from di-t-Butyl Dicarbonate or di-t-Butyl Dithiol Dicarbonates and Amino Acids.

Di-t-butyl dicarbonate and di-t-butyl dithiol dicarbonate effectively prepare N-t-butoxycarbonyl derivatives and their corresponding sulfur analogs, offering potential for selective blocking and deblocking of amino or other groups.

Amino-acids and peptides. XXVII. Further studies on esters of 1-hydroxypiperidine.

The new procedure for obtaining optically pure 1-piperidyl esters from benzyloxycarbonylglycyl-L-phenylalanine yields a high-purity ester, with acetic acid being more effective for condensation reactions.

Citations

Solid-state NMR spectroscopy of the HIV gp41 membrane fusion protein supports intermolecular antiparallel β sheet fusion peptide structure in the final six-helix bundle state.

Solid-state NMR studies reveal that the HIV gp41 membrane fusion protein has intermolecular antiparallel sheet fusion peptide structure in the final six-helix bundle state, supporting the hypothesis that the FP is an autonomous folding domain.

Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

The total synthesis of ()-meloscine was achieved in 19 steps using allenyl azide cycloaddition chemistry, enabling the production of azabicyclo[3.3.0]octadiene and its derivatives.

The HIV fusion peptide adopts intermolecular parallel beta-sheet structure in membranes when stabilized by the adjacent N-terminal heptad repeat: a 13C FTIR study.

The HIV fusion peptide adopts a parallel beta-sheet structure in membranes, potentially playing a role in organizing supramolecular gp41 assembly and inhibiting gp41-induced fusion.

Di‐t‐butyl Dicarbonate

Di-tert-butyl dicarbonate is a flammable liquid with potential for use in organic synthesis, but should be stored in a refrigerator and not exposed to moisture.

Recent Developments, New Trends

The Fmoc group, a base-sensitive but acid-resistant group, revives interest in the acid chloride method for peptide bond formation, with applications in peptide bond formation with urethane-type amine-protecting groups.