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Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-gamma-t-butyl ester-L-glutamyl-N'-(2,4-dimethoxybenzyl)-glycine // Synonyms: (S)-N-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoyl)-N-(2,4-dimethoxybenzyl)glycine, Fmoc-L-Glu(tBu)-(DMB)Gly-OH, Fmoc-Glu(tBu)-DmbGly-OH, Fmoc-Glu(tBu)-(DMB)Gly-OH
|Molecular weight:||632,7 g/mol|
2,4-Dimethoxybenzyl (Dmb) and 2,4,6-trimethoxybenzyl (Tmb) - used for temporary protection of the amide nitrogen of a peptide bond - prevent aggregation during solid phase synthesis. They can also increase peptide cyclization efficiency. Glycine building blocks are available as Fmoc-DmbGly-OH (FAA3390) and Fmoc-TmbGly-OH (FAA3400). For ease of synthesis a dipeptide building block can be used, in order to couple with one process two amino acids. Acidic deprotection methods as normally applied on Wang resin generate the native sequence.
N,O-bisFmoc derivatives of N-(2-hydroxy-4-methoxybenzyl)-amino acids: Useful intermediates in peptide synthesis; T. Johnson, M. Quibell, R. C. Sheppard; J. Pept. Sci. 1995; 1(1): 11-25. https://doi.org/10.1002/psc.310010104.
Innovation and perspectives in solid phase synthesis: peptides, proteins and nucleic acids, biological and biomedical applications; J. F. Kennedy, C. J. Knill; edited by R. Epton; Mayflower Scientific Ltd 1995; 71. https://doi.org/10.1002/pi.1995.210380416.
Proceeding of the 24th EPS; K. Jauch et al; edited by R. Ramage, R. Epton; Mayflower Scientific Ltd 1996; 497.
All-L-Leu-Pro-Leu-Pro: a challenging cyclization; M. El Haddadi, F. Cavelier, E. Vives, A. Azmani, J. Verducci, J. Martinez; J. Pept. Sci. 2000; 6(11): 560-570. https://doi.org/10.1002/1099-1387(200011)6:11<560::AID-PSC275>3.0.CO;2-I.
Efficient synthesis and comparative studies of the arginine and Nomega,Nomega-dimethylarginine forms of the human nucleolin glycine/arginine rich domain; S. Zahariev, C. Guarnaccia, F. Zanutin, A. Pintar, G. Esposito, G. Marvić, B. Krust, A. G. Hovanessian, S. Pongor; J. Pept. Sci. 2005; 11(1): 17-28. https://doi.org/10.1002/psc.577.
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