HCTU

HCTU is an amidinium coupling reagent used in peptide synthesis. It is analogous to HBTU.[1] The HOBt moiety has a chlorine in the 6 position which improves reaction rates and the synthesis of difficult couplings[2][3] HCTU and related reagents containing the 6-chloro-1-hydroxybenzotriazole moiety can be prepared by reaction with TCFH under basic conditions.[4] It can exist in an N-form (guanidinium) or an O-form (uronium), but the N-form is generally considered to be more stable for this class of reagent.[5] In vivo dermal sensitization studies according to OECD 429 confirmed HCTU is a strong skin sensitizer, showing a response at 0.50 wt% in the Local Lymph Node Assay (LLNA) placing it in Globally Harmonized System of Classification and Labelling of Chemicals (GHS) Dermal Sensitization Category 1A.[6]

## References

1. ↑ Marder, Oleg; Shvo, Youval; Albericio, Fernando (2003-08-12). "HCTU and TCTU: New Coupling Reagents — Development and Industrial Aspects" (in en). ChemInform 34 (32). doi:10.1002/chin.200332258. ISSN 1522-2667.
2. ↑ Hood, Christina A.; Fuentes, German; Patel, Hirendra; Page, Karen; Menakuru, Mahendra; Park, Jae H. (2008-01-01). "Fast conventional Fmoc solid-phase peptide synthesis with HCTU" (in en). Journal of Peptide Science 14 (1): 97–101. doi:10.1002/psc.921. ISSN 1099-1387. PMID 17890639.
3. ↑ Sabatino, Giuseppina; Mulinacci, Barbara; Alcaro, Maria C.; Chelli, Mario; Rovero, Paolo; Papini, Anna M. (2002-03-01). "Assessment of new 6-Cl-HOBt based coupling reagents for peptide synthesis. Part 1: Coupling efficiency study" (in en). Letters in Peptide Science 9 (2–3): 119–123. doi:10.1007/bf02576873. ISSN 0929-5666.
4. ↑ El-Faham, Ayman; Albericio, Fernando (2008-04-01). "Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis 1" (in en). The Journal of Organic Chemistry 73 (7): 2731–2737. doi:10.1021/jo702622c. ISSN 0022-3263. PMID 18321124. https://pubs.acs.org/doi/10.1021/jo702622c.
5. ↑ Carpino, Louis A.; Imazumi, Hideko; El-Faham, Ayman; Ferrer, Fernando J.; Zhang, Chongwu; Lee, Yunsub; Foxman, Bruce M.; Henklein, Peter et al. (2002-02-01). "The Uronium/Guanidinium Peptide Coupling Reagents: Finally the True Uronium Salts" (in en). Angewandte Chemie International Edition 41 (3): 441–445. doi:10.1002/1521-3773(20020201)41:3<441::AID-ANIE441>3.0.CO;2-N. PMID 12491372. https://onlinelibrary.wiley.com/doi/10.1002/1521-3773(20020201)41:33.0.CO;2-N.
6. ↑ Graham, Jessica C.; Trejo-Martin, Alejandra; Chilton, Martyn L.; Kostal, Jakub; Bercu, Joel; Beutner, Gregory L.; Bruen, Uma S.; Dolan, David G. et al. (2022-06-20). "An Evaluation of the Occupational Health Hazards of Peptide Couplers" (in en). Chemical Research in Toxicology 35 (6): 1011–1022. doi:10.1021/acs.chemrestox.2c00031. ISSN 0893-228X. PMID 35532537.

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