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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: P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P501c
Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant