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Merck
CN

8.51221

PyAOP

for peptide synthesis, Novabiochem®

Synonym(s):

PyAOP, (7-Azabenzotriazol-1-yloxy)trispyrrolidinophosphonium hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C17H27F6N7OP2
CAS Number:
Molecular Weight:
521.38
UNSPSC Code:
12352101
NACRES:
NA.22
MDL number:
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Product Name

PyAOP, Novabiochem®

SMILES string

F[P-](F)(F)(F)(F)F.[P](=[N+]5CCCC5)(N4CCCC4)(N3CCCC3)O[n]1nnc2c1nccc2

InChI

1S/C17H27N7OP.F6P/c1-2-11-21(10-1)26(22-12-3-4-13-22,23-14-5-6-15-23)25-24-17-16(19-20-24)8-7-9-18-17;1-7(2,3,4,5)6/h7-9H,1-6,10-15H2;/q+1;-1

InChI key

CBZAHNDHLWAZQC-UHFFFAOYSA-N

product line

Novabiochem®

form

powder

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

storage temp.

-10 to -25°C

Quality Level

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

Application

PyAOP can be used as a coupling reagent:
  • In the synthesis of N,N′-substituted acylguanidines by solid-phase peptide synthesis.
  • To facilitate the formation of peptide bonds during the synthesis of cyclic peptide hybrids.

General description

PyAOP is an extremely effective coupling reagent that mediates amide bond formation with the efficiency of HATU but without the risk of guanidine formation, making it the reagent of choice for peptide cyclization.

Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents

Literature references:
[1] F. Albericio, et al. (1997) Tetrahedron Lett., 38, 4853.

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis
F. Albericio, et al.
Tetrahedron Letters, 38, 4853-4853 (1997)
Solid-phase synthesis of N, N?-substituted acylguanidines
Dodd DS and Zhao Y
Tetrahedron Letters, 42, 1259-1262 (2001)
Synthesis of cyclic peptide hybrids with amino acid and nucleobase side-chains
Planas M, et al.
Tetrahedron Letters, 41, 4097-4100 (2000)

Articles

Novabiochem® coupling reagents for in situ activation are fast-reacting and compatible with various amino acids.

Novabiochem®可提供大量的偶联剂用于原位活化。原位活化试剂易于使用 - 即使是利用空间位阻氨基酸,并且它们的使用通常没有副反应。

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