General description

High purity Fmoc-protected amino acid for research and process production of peptides, with very low levels of dipeptide, free-amino acids and acetic acid impurities. The standard derivative for Fmoc SPPS of peptides containing Cys ^[1]. The Trt group is removed with 95% TFA containing 1-5% TIS. Ideally, this derivative should be introduced using the symmetrical anhydride or DIPCDI/HOBt activation ^[2,3] to minimize enantiomerization. If activation with uronium or phosphonium reagents, such as HBTU or PyBOP^®, is to be employed, it is strongly recommended that collidine is used as the base ^[4], as this has been shown to significantly reduce loss of optical integrity during coupling.

Associated Protocols and Technical Articles
Fmoc-amino acids for Peptide Production
Cleavage and Deprotection Protocols for Fmoc SPPS
Fmoc SPPS of Cysteine-Containing Peptides

Literature references

^[1] S. N. McCurdy (1989) Pept. Res., 2, 147.
^[2] T. Kaiser, et al. (1996) Tetrahedron Lett., 37, 1187.
^[3] Y. X. Han, et al. (1997) J. Org. Chem., 62, 4307.
^[4] Y. N. Angell (2002) J. Peptide Res., 5, 292.

Linkage

Replaces: 04-12-1018

Analysis Note

Colour (visual): white to off white
Appearance of substance (visual): powder
Colour index (0,5 M in DMF): ≤ 150 Hazen
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (HPLC): ≥ 99.0 % (a/a)
Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-ß-Ala-Cys (Trt) -OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Cys(Trt)-Cys(Trt)-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Cys-OH (HPLC): ≤ 0.1 % (a/a)
Assay free amino acid (HPLC): ≤ 0.2 %
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 98.0 %
Water (K. F.): ≤ 2.0 %
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.02 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.