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Fmoc-Ser(β-D-GlcNAc(Ac)3)-OH and Fmoc-Thr(β-D-GlcNAc(Ac)3)-OH are useful building blocks for syntheses of peptides containing the GlcNAc modification of serines or threonines. The addition of β-N-acetylglucosamine (GlcNAc) to the hydroxyl group of serines or threonines generating O-linked β-N-acetylglucosamine (O-GlcNAc) serines or threonines is one kind of post-translational modification (PTM) found in proteins (1,2). This O-GlcNAcylation reversible modification directly competes with phosphorylation of these two amino acids (2,3).
Proteins undergo PTM as a mechanism to expand the coding capacity of genes (4). For example, PTMs found in histone "tails" (amino termini) such as acetylation, methylation and phosphorylation affect chromatin structure and exquisitely regulate gene expression (5-10). The use of synthetic histone peptides containing PTMs has helped unraveled some of the mysteries of PTMs and their interaction with downstream effectors. Histone peptides that are 15-20 amino acid long containing biotin either on the N or C-terminus used in pull-down assays has advanced the understanding of these epigenetic relationships (11).
Fmoc-Ser(β-D-GlcNAc(Ac)3)-OH and Fmoc-Thr(β-D-GlcNAc(Ac)3)-OH are compatible with standard protocols in Fmoc solid phase peptide synthesis. Following chain assembly, removal of the acetyl protecting group can be carried out by treatment of the peptidyl resin with methanolic ammonia or sodium methoxide/DMF/methanol, or by treatment of the cleaved peptide with catalytic sodium methoxide in methanol.
At AnaSpec, we are pleased to be a source of premium quality amino acids, whether Fmoc or Boc protected, for PTM peptide syntheses. In addition to glycosylated (GlcNac) serine and threonine, we also provide phosphorylated D or L-serines, D or L-threonines and D-tyrosine; acetylated lysines; methylated (mono, di & tri) lysines and mono, di a/symmetrical methylated arginines and citrullinated arginines.
The Fmoc amino acids that we offer to our customers are the very same amino acids that we use daily in our own manufacturing facilities. We prove the quality of our components in our labs, so you can trust the results in yours.
Visit AnaSpec's website to view our extensive collection of unusual amino acids.
References:
1. Love, DC. & JA. Hanover, Sci STKE 2005, re 13 (2005).
2. Hart, GW. et al. Nature 446, 1017 (2007).
3. Hart, GW. et al. Glycobiol 6, 711 (1996).
4. Walsh, CT. et al. Angew Chem Int Ed 44, 7342 (2005).
5. Grunstein, M. et al. J Cell Sci Suppl 19, 29 (1995).
6. Strahl, BR and CD Allis, Nature 403, 41 (2000).
7. Strahl, BD. et al. Proc Natl Acad Sci 96, 14967 (1999).
8. Jenuwein, T. and CD. Allis Science 293, 1074 (2001).
9. Sterner, DE. et al. Microbiol Mol Biol Rev 64, 435 (2000).
10. Lachner, M. et al. J Cell Sci 116, 2117 (2003).
11. Wysocka, J Methods 40, 339 (2006).
About AnaSpec, EGT Group
AnaSpec, EGT Group is a leading provider of integrated proteomics and genomics solutions™ for worldwide life science research. AnaSpec (anaspec.com) offers expertise in peptides, detection reagents, antibodies, assay kits, amino acids, oligonucleotides, and qPCR MasterMixes. AnaSpec carries a broad product line of biochemicals and reagents for basic research, high-throughput screening and drug discovery. AnaSpec also provides premier custom services including peptide synthesis, antibody production, assay development, fluorescent dyes, and oligonucleotide synthesis. AnaSpec is certified to ISO 9001:2008.
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