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Sigma-Aldrich

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:
3849-21-6
Molecular Weight:
142.11
MDL number:
MFCD00002112
UNSPSC Code:
12352126
EC Index Number:
223-351-3
NACRES:
NA.22
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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

General description

Oxyma Pure (Ethyl cyano(hydroxyimino)acetate) is a non-explosive alternative to the canonical peptide coupling additive N-hydroxybenzotriazole (HOBt).[1] 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.[2]
The generation of toxic hydrogen cyanide (HCN) from the reaction between Oxyma Pure and DIC has been observed.[3] Fortunately, this side reaction can be eliminated by substituting DIC for the more hindered t-butylethylcarbodiimide.[4]

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.[5]
  • As an acidic modifier to prevent aspartimide formation.[6]

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

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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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
A. Caporale, et al.
Peptides, 102, 38-46 (2018)
tert-Butylethylcarbodiimide as an Efficient Substitute for Diisopropylcarbodiimide in Solid-Phase Peptide Synthesis: Understanding the Side Reaction of Carbodiimides with OxymaPure
S. R. Manne, et al.,
Organic Process Research & Development, 26, 2894-2894 (2022)
High-Efficiency Solid Phase Peptide Synthesis (HE-SPPS)
J. Collins , et al.
Organic Letters, 16, 940-940 (2014)
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)
Use of Oxyma as pH modulatory agent to be used in the prevention of base-driven side reactions and its effect on 2-chlorotrityl chloride resin
Ramon S-F, et al.
Journal of Peptide Science, 98, 89-97 (2012)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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