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Alternate names:
(3-amino-2,5-dioxo-1-pyrrolidinyl)acetic acid;
anhydroaspartyl glycine;
aspartimide glycine;
N-(2-aminosuccinyl)glycine

Systematic name:
[(3S)-3-amino-2,5-dioxopyrrolidin-1-yl]acetic acid
Cross-references: ChEBI:45890; PDBHET:ACY; PDBHET:SNN; PDBHET:SUI

Dates:
Created: 31-Mar-2008
Structure revised: 31-Mar-2008
Text changed: 30-Jun-2012

Formula: C 6 H 6 N 2 O 3
Formula weight: #chem 154.13 #phys 154.037842

Correction formula: C 0 H -3 N -1 O 0 #link ASN
Correction weight: #chem -17.03 #phys -17.026549
Based on AA0003+AA0008

Correction formula: C 0 H -2 N 0 O -1 #link ASP
Correction weight: #chem -18.02 #phys -18.010565
Based on AA0004+AA0008

Reference 1:
Authors:
Journal: Eur. J. Biochem. 183, 1-4, 1989
Title: Nomenclature Committee of IUB (NC-IUB) and IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), newsletter 1989.
Cross-references: DOI:10.1111/j.1432-1033.1989.tb14887.x

Reference 2:
Authors: Højrup, P.; Gerola, P.; Hansen, H.F.; Mikkelsen, J.M.; Shahed, A.E.; Knudsen, J.; Roepstorff, P.; Olson, J.M.
Journal: Biochim. Biophys. Acta 1077, 220-224, 1991
Title: The amino acid sequence of a major protein component in the light harvesting complex of the green photosynthetic bacterium Chlorobium limicola f. thiosulfatophilum.
Cross-references: DOI:10.1016/0167-4838(91)90061-4; PMID:2015294
Note: detection of a blocked N-terminal Asn-Gly sequence with a mass loss of "approx. 18 Da"; the formation of (2-aminosuccinimidyl)acetic acid, with a mass loss of 17 Da, would probably block imidazolinone cyclization

Reference 3:
Authors: Hernandez, J.F.; Gagnon, J.; Chiche, L.; Nguyen, T.M.; Andrieu, J.P.; Heitz, A.; Trinh Hong, T.; Pham, T.T.; Le Nguyen, D.
Journal: Biochemistry 39, 5722-5730, 2000
Title: Squash trypsin inhibitors from Momordica cochinchinensis exhibit an atypical macrocyclic structure.
Cross-references: DOI:10.1021/bi9929756 S0006-2960(99)02975-X; PMID:10801322
Note: probable mass spectrometric detection of cyclic anhydride formed from aspartic acid

Reference 4:
Authors: Fitzgerald, P.M.D.; Sharma, N.
Submission: submitted to the Protein Data Bank, July 2001
Description: IMP-1 metallo beta-lactamase from Pseudomonas aeruginosa in complex with a biaryl succinic acid inhibitor (1).
Cross-references: PDB:1JJT
Note: X-ray diffraction, 1.80 angstroms; the cross-link is mentioned in the PDB entry and not in the publication

Reference 5:
Authors: Erskine, P.T.; Coates, L.; Mall, S.; Gill, R.S.; Wood, S.P.; Myles, D.A.A.; Cooper, J.B.
Journal: Protein Sci. 12, 1741-1749, 2003
Title: Atomic resolution analysis of the catalytic site of an aspartic proteinase and an unexpected mode of binding by short peptides.
Cross-references: DOI:10.1110/ps.0305203; PMID:12876323
Note: X-ray diffraction, 0.9 angstroms

Reference 6:
Authors: Coates, L.; Erskine, P.T.; Mall, S.; Gill, R.S.; Wood, S.P.; Myles, D.A.A.; Cooper, J.B.
Submission: submitted to the Protein Data Bank, March 2003
Description: Atomic resolution structure of native endothiapepsin.
Cross-references: PDB:1OEW
Note: X-ray diffraction, 0.9 angstroms

Comment: This cross-link is formed by the condensation of an aspartic acid or asparagine residue with the alpha-amido of the following residue.

Generating Enzyme:
autocatalytic

Sequence code: G, N #link ASN
Conditions: cross-link 1
Cross-references: PSI-MOD:01624

Sequence code: D, G #link ASP
Conditions: cross-link 1
Cross-references: PSI-MOD:00952

Source: natural

Keywords: succinimide ring

UniProt Features
CROSSLNK (2-aminosuccinimidyl)acetic acid (Asn-Gly) #link ASN
CROSSLNK (2-aminosuccinimidyl)acetic acid (Asp-Gly) #link ASP

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