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Fmoc-L-Trp(7-Cl)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-7-chloro-L-tryptophan // Synonyms: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(7-chloro-1H-indol-3-yl)propanoic acid, 7-chloro-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-tryptophan, Fmoc-7-chloro-L-tryptophan,Fmoc-Trp(7-Cl)-OH
- Product code:FAA8475
- CAS No.:2382374-53-8
- Formula:C26H21ClN2O4
- Molecular weight:460.91 g/mol
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description
FAA8475 is a Fmoc protected chloro derivative of L-Tryptophan. Tryptophan is a key residue in many important natural products, e.g. the antibiotic daptomycin. The use of synthetic derivatives of natural amino acids allows to approach a broad variety of molecules enabling the study of structure-activity relationships. Especially the 7-halotryptophan motif is also found in many biologically active natural products.
references
Dynamic Kinetic Resolution for Asymmetric Synthesis of L-Noncanonical Amino Acids from D-Ser Using Tryptophan Synthase and Alanine Racemase; J. Yu, J. Li, X. Gao, S. Zeng, H. Zhang, J. Liu, Q. Jiao; Eur. J. Org. Chem. 2019; 6618-6625. https://doi.org/10.1002/ejoc.201901132
Buchwald Hartwig diversification of unprotected halotryptophans, halotryptophan containing tripeptides and the natural product barettin in aqueous conditions; Y. J. G. Renault, R. Lynch, E. Marelli, S. V. Sharma, C. Pubill-Ulldemolins, J. A. Sharp, C. Cartmell, P. Cárdenas, R. J. M. Goss; Chem. Commun. 2019; 55: 13653-13656. https://doi.org/10.1039/c9cc02554e.
The first one-pot synthesis of L-7-Iodotryptophan from 7-Iodoindole and Serine, and an improved synthesis of other L-7-Halotryptophans; D. R. M. Smith, T. Willemse, D. S. Gkotsi, W. Schepens, B. U. W. Maes, S. Ballet, R. J. M. Goss; Org. Lett. 2014; 16: 2622-2625. https://doi.org/10.1021/ol5007746.
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