26605-36-7

Basic information

• Product Name: N-Succinyl-L-diaminopimelic acid
• Synonyms: Heptanedioic acid, 2-amino-6-[(3-carboxy-1-oxopropyl)amino]-,[S-(R*,R*)]-;Heptanedioic acid,2-amino-6-[(3-carboxy-1-oxopropyl)amino]-, (2S,6S)-;Heptanedioicacid, 2-amino-6-(3-carboxypropionamido)-, L- (8CI);N-Succinyl-L-diaminopimelic acid;2-aMino-6-[(4-hydroxy-4-oxobutanoyl)aMino]heptanedioic
• CAS NO: 26605-36-7
• Molecular Formula: C₁₁H₁₈N₂O₇
• Molecular Weight: 290.2698
• Mol File: 26605-36-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 679°Cat760mmHg
• Flash Point: 364.4°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 3.32E-20mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: N-Succinyl-L-diaminopimelic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-Succinyl-L-diaminopimelic acid(26605-36-7)
• EPA Substance Registry System: N-Succinyl-L-diaminopimelic acid(26605-36-7)

Safety Data

• Hazardous Substances Data: 26605-36-7(Hazardous Substances Data)

Usage

General Description

N-Succinyl-L-diaminopimelic acid is a naturally occurring compound that is a derivative of the amino acid L-lysine. It is an important component of bacterial cell walls, where it functions as a crosslinking agent to provide structural support and rigidity. N-Succinyl-L-diaminopimelic acid is also a key precursor in the biosynthesis of peptidoglycan, a major component of bacterial cell walls. N-Succinyl-L-diaminopimelic acid has been studied for its potential as a target for the development of antibacterial agents, as it plays a critical role in maintaining the integrity of bacterial cell walls. Additionally, it has been used as a biomarker for detecting bacterial infections in clinical samples. Overall, N-Succinyl-L-diaminopimelic acid has important implications for understanding bacterial physiology and for the development of new antibacterial therapies.

InChI:InChI=1/C11H18N2O7/c12-6(10(17)18)2-1-3-7(11(19)20)13-8(14)4-5-9(15)16/h6-7H,1-5,12H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)/t6-,7-/m0/s1

Synthetic route

succinic acid anhydride (108-30-5) + (S,S)-2,6-diaminopimelic acid (14289-34-0) → N-succinyl-L,L-2,6-diaminopimelate (26605-36-7)

Conditions	Yield
With water; potassium carbonate

(S)-2-(3-Carboxy-propionylamino)-6-oxo-heptanedioic acid → N-succinyl-L,L-2,6-diaminopimelate (26605-36-7)

Conditions	Yield
With pyridoxal 5'-phosphate; L-glutamate; NADPH; diaminopimelate aminotransferase from Escherichia coli DH5α In various solvents at 37℃; Enzyme kinetics; Reduction; Amination;

N-succinyl-L,L-2,6-diaminopimelate (26605-36-7) → (S,S)-2,6-diaminopimelic acid (14289-34-0)

Conditions	Yield
With Haemophilus influenzae N-succinyl-L,L-diaminopimelic acid desuccinylase, recombinant, Mr: 41500 pH=7.5; Kinetics; Enzymatic reaction; aq. phosphate buffer;

N-succinyl-L,L-2,6-diaminopimelate (26605-36-7) → (S,S)-2,6-diaminopimelic acid (14289-34-0) + succinate (56-14-4)

Conditions	Yield
With Neisseria meningitidis N-succinyl-L,L-diaminopimelic acid desuccinylase

Upstream product

• 108-30-5 succinic acid anhydride 
• 14289-34-0 (S,S)-2,6-diaminopimelic acid 

Downstream Products

• 14289-34-0 (S,S)-2,6-diaminopimelic acid 

Relevant articles and documents

Synthesis and in vitro enzyme activity of peptide derivatives of bacterial cell wall biosynthesis inhibitors

The enzyme diaminopimelate aminotransferase (DAP-AT) is a good potential target for the design of novel antibacterial agents. We have synthesised a series of peptide hydrazines based on the structure of the natural substrate of DAP-AT. These compounds show varied inhibition properties in vitro vs. DAP-AT from E. coli as well as moderate antimicrobial activity vs. E. coli. Examination of the kinetics of inhibition reveals that hydrazine, as well as the substituted hydrazino-peptides, shows two-phase slow-binding inhibition. Possible mechanisms for inhibition are discussed. The Royal Society of Chemistry 2000.