8.51086
Oxyma Pure
≥99.0% (HPLC), for peptide synthesis, Novabiochem®
Synonym(s):
Oxyma Pure, Ethyl cyano(hydroxyimino)acetate
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About This Item
Empirical Formula (Hill Notation):
C5H6N2O3
CAS Number:
Molecular Weight:
142.11
MDL number:
UNSPSC Code:
12352126
EC Index Number:
223-351-3
NACRES:
NA.22
Recommended Products
product name
Oxyma Pure, Novabiochem®
Quality Level
product line
Novabiochem®
assay
≥99.0% (HPLC)
form
crystalline powder
reaction suitability
reaction type: Coupling Reactions
manufacturer/tradename
Novabiochem®
mp
130-132 °C
application(s)
peptide synthesis
storage temp.
2-8°C
InChI
1S/C5H6N2O3/c1-2-10-5(8)4(3-6)7-9/h9H,2H2,1H3/b7-4+
InChI key
LCFXLZAXGXOXAP-QPJJXVBHSA-N
General description
Oxyma Pure (Ethyl cyano(hydroxyimino)acetate) is a non-explosive alternative to the canonical peptide coupling additive N-hydroxybenzotriazole (HOBt). When used in place of HOBt in carbodiimide-mediated peptide bond formation, it provides products in higher yields with less racemization. The combination of Oxyma Pure/diisopropylcarbodiimide (DIC) has proven to be particularly effective in microwave-assisted peptide synthesis.
The generation of toxic hydrogen cyanide (HCN) from the reaction between Oxyma Pure and DIC has been observed. Fortunately, this side reaction can be eliminated by substituting DIC for the more hindered t-butylethylcarbodiimide.
Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents
Literature references:
[1] R. Subirós-Funosas, et al. (2009) Chem. Eur. J., 15, 9394
[2] J. Collins , et al. (2014) Org . Lett ., 16, 940.
[3] A. D. McFarland (2019) Org. Process Res. Dev., 23, 2099.
[4] S. R. Manne, et al (2022) Org. Process Res. Dev., 26, 2894.
The generation of toxic hydrogen cyanide (HCN) from the reaction between Oxyma Pure and DIC has been observed. Fortunately, this side reaction can be eliminated by substituting DIC for the more hindered t-butylethylcarbodiimide.
Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents
Literature references:
[1] R. Subirós-Funosas, et al. (2009) Chem. Eur. J., 15, 9394
[2] J. Collins , et al. (2014) Org . Lett ., 16, 940.
[3] A. D. McFarland (2019) Org. Process Res. Dev., 23, 2099.
[4] S. R. Manne, et al (2022) Org. Process Res. Dev., 26, 2894.
Application
Further applications of Oxyma Pure:
- Use in the synthesis of difficult peptides.
- As an acidic modifier to prevent aspartimide formation.
Features and Benefits
- Can be used in place of HOBt in carbodiimide-mediated coupling reactions without change of protocol
- It gives results comparable to HOAt in step-wise solid-phase synthesis
- Less epimerization than HOBt in fragment condensation reactions
Analysis Note
Color (visual): white to slight yellow to beige
Appearance of substance (visual): crystalline powder
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Identity (IR): passes test
Solubility (12,5 mmol in 25 ml DMF): clearly soluble
Appearance of substance (visual): crystalline powder
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Identity (IR): passes test
Solubility (12,5 mmol in 25 ml DMF): clearly soluble
Legal Information
Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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tert-Butylethylcarbodiimide as an Efficient Substitute for Diisopropylcarbodiimide in Solid-Phase Peptide Synthesis: Understanding the Side Reaction of Carbodiimides with OxymaPure
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Automatic procedures for the synthesis of difficult peptides using oxyma as activating reagent: A comparative study on the use of bases and on different deprotection and agitation conditions
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High-Efficiency Solid Phase Peptide Synthesis (HE-SPPS)
J. Collins , et al.
Organic Letters, 16, 940-940 (2014)
Oxyma: An Efficient Additive for Peptide Synthesis to Replace the Benzotriazole-Based HOBt and HOAt with a Lower Risk of Explosion
R. Subiros-Funosas, et al.
Chemistry?A European Journal , 15, 9394-9394 (2009)
Generation of Hydrogen Cyanide from the Reaction of Oxyma (Ethyl Cyano(hydroxyimino)acetate) and DIC (Diisopropylcarbodiimide)
A. D. McFarland
Organic Process Research & Development, 23, 2099-2099 (2019)
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