|Fmoc-TOAC-OH & Fmoc-Lys(Nvoc)-OH
As one of the world’s most trusted suppliers
of custom peptides, AnaSpec has a well-earned reputation for expertise in
the field of peptide chemistry. We are pleased to introduce two novel amino
acids that offer additional tools and functionality for peptide chemists like
acid) is a nitroxide spin-label used in electron spin resonance, ESR (also
known as electron paramagnetic resonance, EPR) studies.1,2 This
Ca-tetrasubstituted cyclic structure unnatural amino acid is an
excellent and relatively rigid ESR probe, making it a useful tool in the study
of peptide backbone conformational properties.2 TOAC has been
shown to be an effective ß-turn and 310/a-helix promoter in peptides
as well as a fluorescence quencher. Publications have reported the use of
Fmoc-TOAC-OH in the synthesis of internally containing spin probe peptide sequence,3,4
which was previously not possible with BOC protected TOAC. The
incorporation of this amino acid has also been reported in the synthesis of
a biologically active hormone.2
4, 5-dimethoxy-2-nitrobenzyloxycarbonyl (Nvoc) is a photocleavable
protecting group used for side-chain amine protection or for a-amine blocking.
Compared with another photocleavable protecting group Z(2-NO2),
Nvoc deprotection gave a higher yield under similar condition. Fmoc-Lys(Nvoc)-OH
has been used in the solid phase peptide synthesis of selectively functionalized
HIV and caged peptides.5,6 The removal of the Nvoc group, from
the protected peptide, is compatible with the presence of a reactive maleimide
linker which is useful for conjugation of peptides to proteins containing
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Heavy Isotope Labeled Resins and Amino Acids:
Custom Peptide Synthesis
with Unusual Amino Acids
- Rassat, A. and P. Rey. Bull. Soc. Chim. Fr. 3, 815 (1967).
- Barbosa, SR. et al. FEBS Lett. 446, 45 (1999).
- Marchetto, R. et al. J. Am.
Chem. Soc. 115, 11042 (1993).
- Martin, L. et al. J. Pept.
Res. 58, 424 (2001).
- Rusiecki, VK. & SA. Warne
Bioorg. Med. Chem. Lett., 3, 707 (1993).
- Tatsu, Y. et al. In “Dynamic Studies
in Biology: Phototriggers, Photoswitches and Caged. Wiley-VCH (2005)