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Chemical name: (2R,4S)-N-alpha-t-Butyloxycarbonyl-4-(9-fluorenylmethyloxycarbonyl)amino-D-proline // Synonyms: trans-Boc-D-Pro(4-NHFmoc)-OH, N-Boc-trans-4-N-Fmoc-amino-D-proline, (2R,4S)-Fmoc-4-amino-1-Boc-pyrrolidine-2-carboxylic acid, (2R,4S)-1-Boc-4-(Fmoc-amino)-pyrrolidine-2-carboxylic acid, (2R,4S)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(t-butoxycarbonyl)pyrrolidine-2-carboxylic acid
|Molecular weight:||452,51 g/mol|
This building block is reported as a sort of a,g-locked g-aminobutanoic acid (GABA) surrogate. The 4-amino and 2-carboxy group can easily be used for the incorporation into peptide sequences leaving the Na-proline site free for covalent bonding to various tethers and functional units.
Typically, peptide bonds are in trans conformation. Residues at the pyrrolidine ring of proline induce cis-/ trans-amide bond conformation through steric and/or electronic effects.
Thus, BAA4570 and its (2R,4R)-derivative BAA3690 can be used for conformational studies and for tuning pharmaceutical and biological properties of peptides.
Discovery of Subnanomolar Arginine-Glycine-Aspartate-Based anb3/anb5 Integrin Binders Embedding 4-Aminoproline Residues; F. Zanardi, P. Burreddu, G. Rassu, L. Auzzas, L. Battistini, C. Curti, A. Sartori, G. Nicastro, G. Menchi, N. Cini, A. Bottonoceti, S. Raspanti, and G. Casiraghi; J. Med. Chem. 2008; 51: 1771-1782; https://doi.org/10.1021/jm701214z
The cis-4-Amino-L-proline Residue as a Scaffold for the Synhesis of Cyclic and Linear Endomorphin-2 Analogues; A. Mollica, F. Pinnen, A. Stefanucci, F. Feliciani, C. Campestre, L. Mannia, A. P. Sobolev, G. Lucente, P. Davis, J. Lai, S.-W. Ma, F. Porreca, V. J. Hruby; J. Med. Chem. 2012; 55: 3027-3035; https://doi.org/10.1021/jm201402v
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