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Sigma-Aldrich

Fmoc-TOAC-OH

Novabiochem®

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Synonym(s):
Fmoc-TOAC-OH, 2,2,6,6-Tetramethylpiperidine-N-oxyl-4-(9-fluorenylmethyloxycarbonyl-amino)-4-carboxylic acid
Empirical Formula (Hill Notation):
C25H29N2O5
CAS Number:
93372-25-9
Molecular Weight:
437.51

Quality Level

200

product line

Novabiochem®

Assay

≥98.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

InChI

1S/C25H29N2O5/c1-23(2)14-25(21(28)29,15-24(3,4)27(23)31)26-22(30)32-13-20-18-11-7-5-9-16(18)17-10-6-8-12-19(17)20/h5-12,20H,13-15H2,1-4H3,(H,26,30)(H,28,29)

InChI key

FAQWDTRJLKQJBN-UHFFFAOYSA-N

Related Categories

General description

Fmoc-TOAC-OH is a useful tool for the incorporation of the ESR spin-label TOAC into peptide sequences [1] by Fmoc SPPS. Incorporation of this derivative and the following residue is best achieved using HATU activation. TFA/water/TIS should be used for cleavage of TOAC-containing peptides. The use of EDT should be avoided as it can cause permanent reduction of the nitroxide radical [2]. Following cleavage, the TOAC peptide should be treated with aqueous ammonia in air to regenerate the nitroxide from the hydroxylamine that is generated by the TFA treatment.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Chromogenic Labeling of Synthetic Peptides

Literature references

[1] R. Marchetto, et at. (1993) J. Am. Chem. Soc., 115, 11042.
[2] L. Martin, et al. (2001) J. Pept. Res., 58, 424.

Analysis Note

Color (visual): white to yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 98.0 % (a/a)

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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