PyBOP

Also known as benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate

PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis. It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. It is a substitute for the BOP reagent that avoids the formation of the carcinogenic waste product HMPA. Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyBOP is potentially explosive.

Chemical data

Formula: C18H28F6N6OP2
Molecular weight: 520.4 g/mol
IUPAC name: benzotriazol-1-yloxy(tripyrrolidin-1-yl)phosphanium hexafluorophosphate
SMILES: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
InChIKey: VIAFLMPQBHAMLI-UHFFFAOYSA-N
Polar surface area: 49.7 Å²
H-bond donors: 0
H-bond acceptors: 13
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Mass: 520.170402

Show 3 more facts

canonical SMILES: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
chemical formula: C₁₈H₂₈F₆N₆OP₂
Commons category: PyBOP

Sources (2)

via Wikidata · CC0

Article · 日本語

PyBOP は、ペプチド合成に用いられる脱水縮合剤のひとつ。ヘキサフルオロリン酸（ベンゾトリアゾール-1-イルオキシ）トリピロリジノホスホニウムのことで、"PyBOP" はドイツのメルク社の登録商標。PyBOP は BOP の誘導体のひとつで、BOP が反応後に毒性の HMPA を出してしまう欠点が、PyBOP では避けられる。

Abstract from DBpedia / Wikipedia · CC BY-SA