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915823

Sigma-Aldrich

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

≥95%

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

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About This Item

Empirical Formula (Hill Notation):
C24H25NO4S
Molecular Weight:
423.52
UNSPSC Code:
12352209

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

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Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

915823-VAR:
915823-250MG:
915823-BULK:
915823-500MG:

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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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