Skip to Content
MilliporeSigma

8.51086

Oxyma Pure

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

Synonym(s):

Oxyma Pure, Ethyl cyano(hydroxyimino)acetate

Sign In to View Organizational & Contract Pricing.

Select a Size

25 G

$43.50

100 G

$127.00

250 G

$232.00

500 G

$408.00

1 KG

$709.00

5 KG

$3,070.00

$43.50


Estimated to ship TODAYDetails


Request a Bulk Order

About This Item

Empirical Formula (Hill Notation):
C5H6N2O3
CAS Number:
Molecular Weight:
142.11
UNSPSC Code:
12352126
EC Index Number:
223-351-3
NACRES:
NA.22
MDL number:

Skip To

Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Oxyma Pure, Novabiochem®

InChI

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

InChI key

LCFXLZAXGXOXAP-QPJJXVBHSA-N

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

Quality Level

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
8.512128.510958.51094
form

crystalline powder

form

powder

form

powder

form

powder

assay

≥99.0% (HPLC)

assay

-

assay

≥99.0% (HPLC)

assay

≥98.0% (HPLC)

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

15-25°C

storage temp.

2-8°C

mp

130-132 °C

mp

145-155 °C

mp

-

mp

-

Quality Level

300

Quality Level

200

Quality Level

300

Quality Level

200

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

Application

Further applications of Oxyma Pure:
  • Use in the synthesis of difficult peptides.[1]
  • As an acidic modifier to prevent aspartimide formation.[2]

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

General description

Oxyma Pure (Ethyl cyano(hydroxyimino)acetate) is a non-explosive alternative to the canonical peptide coupling additive N-hydroxybenzotriazole (HOBt).[3] 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.[4]
The generation of toxic hydrogen cyanide (HCN) from the reaction between Oxyma Pure and DIC has been observed.[5] Fortunately, this side reaction can be eliminated by substituting DIC for the more hindered t-butylethylcarbodiimide.[6]

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.

Legal Information

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

Storage Class

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)

Questions

1–2 of 2 Questions  
  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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service