Q-1610
3-(4-Methoxy-benzylsulfanyl)-3-methyl-butyric acid
Synonym:
S-(4-Methoxybenzyl)-deamino-penicillamine
| C13H18O3S | Mr: 254.35 | [268219-99-4] |
| Longterm storage temperature: | +5 ± 3 °C | C13H18O3S |
S-protected derivative for the introduction of a deamino-penicillamine residue. Building block for the preparation of oxytocin and vasopressin antagonists. Peptide thioesters for chemical ligation may be obtained by Fmoc-SPPS using a deaminopenicillamine-derived linker, as premature cleavage during Fmoc removal is inhibited by steric hindrance. Tegge et al. developed a deaminopenicillamine-based disulfide linker for the Fmoc-SPPS of cyclic Cys-containing peptides.
Literature:
D.Gazis et al., Int. J. Peptide Protein Res., 23, 78 (1984)
M.Manning et al., J. Med. Chem., 28, 1485 (1985)
M.Manning et al., J. Med. Chem., 32, 382 (1989)
X.Li et al., Tetrahedron Lett., 39, 8669 (1998)
W.Tegge et al., J. Pept. Sci., 13, 693 (2007)
D.Gazis et al., Int. J. Peptide Protein Res., 23, 78 (1984)
M.Manning et al., J. Med. Chem., 28, 1485 (1985)
M.Manning et al., J. Med. Chem., 32, 382 (1989)
X.Li et al., Tetrahedron Lett., 39, 8669 (1998)
W.Tegge et al., J. Pept. Sci., 13, 693 (2007)
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Family Description:
Corresponds to β,β-dimethylcysteine or β-mercaptovaline. For an S-protected derivative of deamino-penicillamine please see Q-1610.
The rigidity of disulfide bridges can be increased by replacing Cys by Pen. Pen analogs of enkephalins, RGD-peptides, urotensin and further active peptides with improved potency and/or selectivity have been described.
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