A byproduct in solid-phase peptide synthesis
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(S)-Aspartimide

Item No. 31700

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3S-amino-2,5-pyrrolidinedione
CAS Number
73537-92-5
Molecular Formula
C4H6N2O2
Formula Weight
Purity
≥95%
A solid
DMSO: SolubleMethanol: Soluble
SMILES
N[C@@H]1C(NC(C1)=O)=O
InChi Code
InChI=1S/C4H6N2O2/c5-2-1-3(7)6-4(2)8/h2H,1,5H2,(H,6,7,8)/t2-/m0/s1
InChi Key
YDNMHDRXNOHCJH-REOHCLBHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (S)-Aspartimide is a byproduct formed during solid-phase peptide synthesis (SPPS) of aspartic acid-containing peptides.1 Aspartimide is formed by cyclization of aspartic acid during Fmoc removal or peptide coupling.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ruczyński, J., Lewandowska, B., Mucha, P., et al. Problem of aspartimide formation in Fmoc-based solid-phase peptide synthesis using Dmab group to protect side chain of aspartic acid. J. Pept. Sci. 14(3), 335-341 (2008).

    2. Neumann, K., Farnung, J., Baldauf, S., et al. Prevention of aspartimide formation during peptide synthesis using cyanosulfurylides as carboxylic acid-protecting groups. Nat. Commun. 11(1), 982 (2020).