8.51086

Oxyma Pure

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

• Synonym(s): Oxyma Pure, Ethyl cyano(hydroxyimino)acetate
• Empirical Formula (Hill Notation): C₅H₆N₂O₃
• CAS Number: 3849-21-6
• Molecular Weight: 142.11
• MDL number: MFCD00002112
• UNSPSC Code: 12352126
• EC Index Number: 223-351-3
• NACRES: NA.22

Properties

• product name: Oxyma Pure, Novabiochem^®
• Quality Level: 300
• 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

Description

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.

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

Legal Information

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable