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900606

Sigma-Aldrich

Fmoc-Trp-BODIPY

≥95%

Synonym(s):
Trp-BODIPY
Empirical Formula (Hill Notation):
C45H39BF2N4O4
Molecular Weight:
748.62

Quality Level

assay

≥95%

form

powder

functional group

Fmoc

Application

This compound is an Fmoc-labeled amino acid of tryptophan attached to a BODIPY dye through a spacer-free C-C linkage that can be used in solid phase peptide synthesis (SPPS). Research presented in Mendive-Tapia et al. tested the incorporation of the fluorescent amino acid into an anti-fungal peptide with two tryptophans by replacing either one or both of the residues. The three peptides showed enhanced fluorescence with increasing hydrophobicity of the environment. The peptides also maintained binding to Aspergillus fumigatus and could be detected by fluorescence imaging. That same publication showed that a cyclic version of the peptide containing a single fluorescent amino acid was more resistant to proteolysis than the linear peptide and still useful for imaging. The amino acid can be incorporated during standard conditions for SPPS and can also tolerate mildly acidic conditions of 1% trifluoroacetic acid allowing use of acid-labile solid supports. This amino acid should enable fluorescence detection of peptides for use in a variety of applications.

Packaging

100 mg in glass insert

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Spacer-free BODIPY fluorogens in antimicrobial peptides for direct imaging of fungal infection in human tissue.
Tapia ML, et al.
Nature Communications, 7, 10940-10940 (2016)

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