HOBt (anhydrous) is a heterocycle most often used as a catalytic or stoichiometric agent to accelerate nucleophilic acyl substitution reactions, particularly amidations [1]. HOBt is able to propagate a detonation when a strong booster is used [2]. HOBt plays a significant role in reducing the racemization during peptide synthesis and is regularly used as a coupling additive [3]. In the H2O-THF solvent, HOBt can be used as an activator to synthesize small peptides without the use of protecting groups and shorten the reaction time[4].
References:
[1] Treitler D S, Marriott A S, Chadwick J, et al. Mutagenic impurities in 1-hydroxybenzotriazole (HOBt)[J]. Organic Process Research & Development, 2019, 23(11): 2562-2566
[2] Wehrstedt K D, Wandrey P A, Heitkamp D. Explosive properties of 1-hydroxybenzotriazoles[J]. Journal of hazardous materials, 2005, 126(1-3): 1-7.
[3] Mali S M, Kumar M G, Katariya M M, et al. HBTU mediated 1-hydroxybenzotriazole (HOBt) conjugate addition: synthesis and stereochemical analysis of β-benzotriazole N-oxide substituted γ-amino acids and hybrid peptides[J]. Organic & Biomolecular Chemistry, 2014, 12(42): 8462-8472.
[4] Herrera-Guzmán K, Jaime-Vasconcelos M Á, Torales E, et al. A practical method for the synthesis of small peptides using DCC and HOBt as activators in H 2 O–THF while avoiding the use of protecting groups[J]. RSC advances, 2024, 14(54): 39968-39976.
HOBt (anhydrous)是一种杂环化合物，最常用作催化或化学计量试剂，以加速亲核酰基取代反应，特别是酰胺化反应[1]。HOBt在强引爆剂的作用下能够引发爆炸[2]。HOBt在减少肽合成过程中的外消旋方面起着重要作用，并常规用作偶联添加剂[3]。在H2O-THF溶剂中，HOBt可作为活化剂，用于无需保护基的小肽合成，并缩短反应时间[4]。