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Sigma-Aldrich

PyOxim

≥99.0% (HPLC), for peptide synthesis, Novabiochem®

Synonym(s):

PyOxim, 1-Cyano-2-ethoxy-2-oxoethylideneaminooxy-tris-pyrrolidino-phosphonium hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C17H29F6N5O3P2
CAS Number:
153433-21-7
Molecular Weight:
527.38
MDL number:
MFCD18643381
UNSPSC Code:
12352126
NACRES:
NA.22

product name

PyOxim, Novabiochem®

Quality Level

300

product line

Novabiochem®

Assay

≥99.0% (HPLC)

form

powder

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

storage temp.

15-25°C

InChI

1S/C17H29N5O3P.F6P/c1-2-24-17(23)16(15-18)19-25-26(20-9-3-4-10-20,21-11-5-6-12-21)22-13-7-8-14-22;1-7(2,3,4,5)6/h2-14H2,1H3;/q+1;-1/b19-16+;

InChI key

RDWDVLFMPFUBDV-PXMDEAMVSA-N

Related Categories

General description

PyOxim [1] is a novel reagent which mediates coupling reactions with efficiencies superior to HATU and PyBOP and comparable to COMU. It is has excellent solubility in DMF and is stable in solution under an inert atmosphere for two days. Unlike HATU and HBTU, it cannot cause chain terminating side reactions and is, therefore, ideal for the synthesis of cyclic peptides. Furthermore, it is not explosive under normal operating conditions and is less likely to exhibit allergenicity compared to other coupling reagents.


Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents

Literature references

[1] R. Subiros-Funosas, et al. (2010) Org. Biomol. Chem., 8, 3665.

Features and Benefits

  • Mediates coupling with superior efficiency to PyBOP, TBTU, and HCTU
  • Mediates coupling with low racemization or epimerization
  • Ideal for fragment condensation and synthesis of cyclic peptides as the reagent cannot cause guanidinylation
  • Excellent solubility in DMF and NMP

Analysis Note

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

Legal Information

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

Storage Class Code

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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Articles

Peptide Coupling Reagents Guide

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

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