(R)-Aspartimide | CAS#404887-22-5 | SPPS byproduct

MedKoo Cat#: 463368 | Name: (R)-Aspartimide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

(R)-Aspartimide is a byproduct formed during solid-phase peptide synthesis (SPPS) of aspartic acid-containing peptides. Aspartimide is formed by cyclization of aspartic acid during Fmoc removal or peptide coupling.

Chemical Structure

(R)-Aspartimide

CAS#404887-22-5

Theoretical Analysis

MedKoo Cat#: 463368

Name: (R)-Aspartimide

CAS#: 404887-22-5

Chemical Formula: C4H6N2O2

Exact Mass: 114.0429

Molecular Weight: 114.10

Elemental Analysis: C, 42.11; H, 5.30; N, 24.55; O, 28.04

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 650.00	2 Weeks

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Related CAS #

No Data

Synonym

(R)-Aspartimide; (R) Aspartimide;

IUPAC/Chemical Name

(R)-3-aminopyrrolidine-2,5-dione

InChi Key

YDNMHDRXNOHCJH-UWTATZPHSA-N

InChi Code

InChI=1S/C4H6N2O2/c5-2-1-3(7)6-4(2)8/h2H,1,5H2,(H,6,7,8)/t2-/m1/s1

SMILES Code

N[C@H]1C(NC(C1)=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 114.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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Prevention of aspartimide formation during peptide synthesis using cyanosulfurylides as carboxylic acid-protecting groups. Nat Commun. 2020 Feb 20;11(1):982. doi: 10.1038/s41467-020-14755-6. PMID: 32080186; PMCID: PMC7033154. 5: Samson D, Rentsch D, Minuth M, Meier T, Loidl G. The aspartimide problem persists: Fluorenylmethyloxycarbonyl-solid-phase peptide synthesis (Fmoc-SPPS) chain termination due to formation of N-terminal piperazine-2,5-diones. J Pept Sci. 2019 Jul;25(7):e3193. doi: 10.1002/psc.3193. PMID: 31309675; PMCID: PMC6772008. 6: Scala MC, Spensiero A, Pepe G, Bertamino A, Carotenuto A, Grieco P, Novellino E, Gomez-Monterrey IM, Campiglia P, Sala M. Investigation on side-product formation during the synthesis of a lactoferrin-derived lactam-bridged cyclic peptide. Amino Acids. 2018 Oct;50(10):1367-1375. doi: 10.1007/s00726-018-2612-9. Epub 2018 Jul 4. PMID: 29974257. 7: Gandioso A, Cano M, Massaguer A, Marchán V. A Green Light-Triggerable RGD Peptide for Photocontrolled Targeted Drug Delivery: Synthesis and Photolysis Studies. J Org Chem. 2016 Dec 2;81(23):11556-11564. doi: 10.1021/acs.joc.6b02415. Epub 2016 Nov 16. PMID: 27934458. 8: Abdel-Aal AB, Papageorgiou G, Raz R, Quibell M, Burlina F, Offer J. A backbone amide protecting group for overcoming difficult sequences and suppressing aspartimide formation. J Pept Sci. 2016 May;22(5):360-7. doi: 10.1002/psc.2877. Epub 2016 Apr 18. PMID: 27086749; PMCID: PMC5074248. 9: Debnath K, Mandal K, Jana NR. Phase Transfer and Surface Functionalization of Hydrophobic Nanoparticle using Amphiphilic Poly(amino acid). Langmuir. 2016 Mar 22;32(11):2798-807. doi: 10.1021/acs.langmuir.6b00282. Epub 2016 Mar 7. PMID: 26928391. 10: Behrendt R, White P, Offer J. Advances in Fmoc solid-phase peptide synthesis. J Pept Sci. 2016 Jan;22(1):4-27. doi: 10.1002/psc.2836. PMID: 26785684; PMCID: PMC4745034. 11: Behrendt R, Huber S, White P. Preventing aspartimide formation in Fmoc SPPS of Asp-Gly containing peptides--practical aspects of new trialkylcarbinol based protecting groups. J Pept Sci. 2016 Feb;22(2):92-7. doi: 10.1002/psc.2844. Epub 2016 Jan 11. PMID: 26751703. 12: Tailhades J, Sethi A, Petrie EJ, Gooley PR, Bathgate RA, Wade JD, Hossain MA. Native Chemical Ligation to Minimize Aspartimide Formation during Chemical Synthesis of Small LDLa Protein. Chemistry. 2016 Jan 18;22(3):1146-51. doi: 10.1002/chem.201503599. Epub 2015 Nov 27. PMID: 26612092. 13: Behrendt R, Huber S, Martí R, White P. New t-butyl based aspartate protecting groups preventing aspartimide formation in Fmoc SPPS. J Pept Sci. 2015 Aug;21(8):680-7. doi: 10.1002/psc.2790. Epub 2015 Jun 15. PMID: 26077723. 14: Reimann O, Glanz M, Hackenberger CP. Native chemical ligation between asparagine and valine: application and limitations for the synthesis of tri- phosphorylated C-terminal tau. Bioorg Med Chem. 2015 Jun 15;23(12):2890-4. doi: 10.1016/j.bmc.2015.03.028. Epub 2015 Mar 17. PMID: 25882528. 15: Dall E, Fegg JC, Briza P, Brandstetter H. Structure and mechanism of an aspartimide-dependent peptide ligase in human legumain. Angew Chem Int Ed Engl. 2015 Mar 2;54(10):2917-21. doi: 10.1002/anie.201409135. Epub 2015 Jan 28. PMID: 25630877; PMCID: PMC4506564. 16: Mong SK, Vinogradov AA, Simon MD, Pentelute BL. Rapid total synthesis of DARPin pE59 and barnase. Chembiochem. 2014 Mar 21;15(5):721-33. doi: 10.1002/cbic.201300797. Epub 2014 Mar 11. PMID: 24616257; PMCID: PMC4045705. 17: Chen CC, Rajagopal B, Liu XY, Chen KL, Tyan YC, Lin F, Lin PC. A mild removal of Fmoc group using sodium azide. Amino Acids. 2014 Feb;46(2):367-74. doi: 10.1007/s00726-013-1625-7. Epub 2013 Dec 5. PMID: 24306456. 18: Vanier GS. Microwave-assisted solid-phase peptide synthesis based on the Fmoc protecting group strategy (CEM). 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