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O-(1H-Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate is used as a coupling reagent for solid-phase peptide synthesis. It has been shown to effectively suppress racemization.
Peptide coupling reagent giving high yields with minimal racemization: Synthesis, 572 (1984). See Appendix 6.
Yoshida, M.; Sasahara, K. I.; Doi, T. Total synthesis of cyclodepsipeptide spiruchostatin A on silyl-linked polymer-support. Tetrahedron 2015, 71 (40), 7647-7653.
Buba, A. E.; Löwe, H.; Kunz, H. Fluorenylmethoxycarbonyl-Protected O-Glycosyl-N-methyl Amino Acids: Building Blocks for the Synthesis of Conformationally Tuned Glycopeptide Antigens. Eur. J. Org. Chem. 2015, 2015 (26), 5764-5774.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.