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776874

Sigma-Aldrich

K-Oxyma

97%

Synonym(s):

2-Cyano-2-(hydroxyimino)acetic acid ethyl ester, potassium salt, Ethyl (hydroxyimino)cyanoacetate potassium salt

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About This Item

Empirical Formula (Hill Notation):
C5H5KN2O3
CAS Number:
Molecular Weight:
180.20
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

powder

reaction suitability

reaction type: Addition Reactions

mp

141-147

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

CCOC(/C(C#N)=N/[O-])=O.[K+]

InChI

1S/C5H6N2O3.K/c1-2-10-5(8)4(3-6)7-9;/h9H,2H2,1H3;/q;+1/p-1/b7-4+;

InChI key

ZFBMUWGNRJITLS-KQGICBIGSA-M

Application

  • Non-explosive replacement for HOBt and HOAt with at least comparable performance to HOAt
  • Outperforms HOAt in sterically demanding peptide bond formations
  • Compatible with carbodiimide-mediated; solution and solid phase peptide coupling;
  • Less epimerization than HOBt in fragment condensation reactions
  • K-salt especially useful in peptide coupling on mild acid-labile resins such as 2-chlorotrityl; leading to minimal to no cleavage of the peptide from the resin due to its more alkaline character
  • K-salt has a higher melting point than OxymaPure

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Subiros-Funosas; R. et al
Chemistry (Weinheim An Der Bergstrasse, Germany), 15, 9394-9403 (2009)

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