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915823

Sigma-Aldrich

Fmoc-Cys(2,4-hexadiene)-OH

≥95%

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Synonym(s):
N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-S-((2E,4E)-hexa-2,4-dien-1-yl)-L-cysteine, Diene-containing cysteine for peptide macrocylization
Empirical Formula (Hill Notation):
C24H25NO4S
Molecular Weight:
423.52

Assay

≥95%

form

solid

mp

91-96 °C

storage temp.

−20°C

Application

Fmoc-Cys(2,4-hexadiene)-OH is a diene-containing amino acid developed in the Moellering lab for the preparation of Diels-Alder-cyclized peptides for macrocyclization and peptide stabilization. Peptide macrocycles are of increasing interest for improving peptide bioactivity and properties as well as their potential to study, stabilize, or inhibit protein-protein interactions (PPIs).

Other Notes

Versatile Peptide Macrocyclization with Diels-Alder Cycloadditions

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Jeffrey E Montgomery et al.
Journal of the American Chemical Society, 141(41), 16374-16381 (2019-09-17)
Macrocyclization can improve bioactive peptide ligands through preorganization of molecular topology, leading to improvement of pharmacologic properties like binding affinity, cell permeability, and metabolic stability. Here we demonstrate that Diels-Alder [4 + 2] cycloadditions can be harnessed for peptide macrocyclization

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