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21.11.1.1 Method 1: α-Amino Protection

DOI: 10.1055/sos-SD-021-00693

Lubell, W. D.; Blankenship, J. W.; Fridkin, G.; Kaul, R., Science of Synthesis, (2005) 21, 715.

Many of the common amine protecting groups in use today have been developed to address issues in peptide science. Among the large number of amine protecting groups that have been employed in peptide synthesis, urethane-based protecting groups have been shown repeatedly to have superior properties with respect to their ease of handling, incorporation, and removal, as well as their ability to protect the α-amino acid configuration. Urethanes are typically introduced by coupling the amino acid to either a chloroformate, dicarbonate, succinimido carbonate, or an azidoformate in the presence of a base (‌Scheme 1‌), such as sodium carbonate, sodium hydrogen carbonate, or triethylamine, in a mixed solvent system such as dioxane/water or tetrahydrofuran/water, so-called Schotten–Baumann conditions.[‌22‌,‌23‌]

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References

[22] Meeeeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888.
[23] Meeeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888.
[24] Meeeeeeeee, M.; Meeeeeee, M.; Meeeeeeee, M., Meee Meee. Meeee., (8888) 88, 8888.
[25] Meeeeeee, M., Meee. Meee. Meee, (8888) 88, 888.
[26] Meeeeeeee, M. M.; Meeeeeeeee, M. M.; Meee, M. M.; Meeeee, M. M. M.; Meeé, M. M.; Meeeee, M. M.; eee Meeeeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888.
[27] Meeeee, M. M.; Meeeeee, M. M., MMM; Meee, M. M.; Meeee, M. M.; Meeeeeee, M. M., Me.; Meeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888.
[28] Meeeeeee, M.; Mee, M.; Meeeeee, M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888.
[29] Meee, M. M.; Meeeeee, M.; Meeeeeee, M. M.; Meeeeee, M. M., Meee. Mee., (8888) 8, 888.
[30] Meeeeeeeeeee, M. M.; Meeeeeeeeeee, M.; Meeeee Meee, M. M., Meeeee M. Meee., Meee. M, (8888) 88, 888.
[31] Meeeeeee, M.; Meeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888.
[32] Mee-Meeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888.
[33] Meeeeeeeee, M.; Meeeeeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888.
[34] Meeeeeee, M.; Meeeeeeee, M.; Meeeee, M., Meee. Mee., (8888) 88, 888.
[35] Meeeé, M., Meeeeeeeeee, (8888) 88, 8888.
[36] Meee, M.; Meeeeeee, M., Meeee. Meee., (8888) 88, 88; Meeee. Meee. Mee. Me. Meee., (8888) 88, 88.
[37] Meeeeeee, M.; Meeeeeeee, M.-M.; Meeeeeee, M.; Meeeé, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888.
[38] Meeeeeeää, M.; Meeeeee, M.; Meeeeee, M. M.; Meeeeeeeee, M.; Meeeeeee, M.; Meee, M., MMMM Meee., (8888) 888, 888.
[39] Meeeeee, M. M.; Mee, M.-M.; Mee, M.-M.; Meeeeee, M. M., Meeeeee Meee. Meee., (8888) 8, 888.

Meeeeee Meeeeeeeeee

  • 8.Meeeee-Meee, (8888) 88/8, 88.
  • 8.Meeeee-Meee, (8888) M 88e, 88.
  • 8.Meeeee-Meee, (8888) M 88e, 88.

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