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Fmoc-L-Ala(3-Cl)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-3-chloro-L-alanine // Synonyms: (R)-2-[(9-Fluorenylmethyloxycarbonyl)amino]-3-chloro-propionic acid, Fmoc-beta-chloro-L-alanine, Fmoc-3-chloro-L-alanine, Fmoc-Ala(3-Cl)-OH
- Product code:FAA3170
- CAS No.:212651-52-0
- Formula:C18H16ClNO4
- Molecular weight:345.78 g/mol
- Purity :min. 98%
- Enantiomeric Purity:min. 99,7%
Starting at $187.50
description
The Chlorine function in this building block is labile and reactive. Depending on reaction conditions, it is prone to nucleophilic substitution or to elimination. Thus, it is not primarily a building block to permanently introduce 3-Chloroalanine into a peptide, but rather to use the function for further modification such as cyclic peptide ring closure or introduction of Dehydroalanine. However, there are also publications (see below) reporting introduction of 3-Chloroalanine into peptides without elimination.
references
Halogen Bonding: A Powerful Tool for Modulation of Peptide Conformation; E. Danelius, H. Andersson, P. Jarvoll, K. Lood, J. Gräfenstein, M. Erdélyi; Biochemistry 2017; 56: 3265-3272. https://doi.org/10.1021/acs.biochem.7b00429
Cyclization of Peptides by using Selenolanthionine Bridges; A. D. de Araujo, M. Mobli, G. F. King, P. F. Alewood; Angew. Chem. Int. Ed. 2012; 51: 10298-10302. https://doi.org/10.1002/anie.201204229
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