(2S,6S)-(+)-2,6-diaminopimelic acid, CAS No. 14289-34-0

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14289-34-0

Catalog No. EBD937329

CAS 14289-34-0

Name (2S,6S)-(+)-2,6-diaminopimelic acid

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Basic Information

Synonyms: (6S,2S)-Diaminopimelicacid Heptanedioicacid,2,6-diamino-,(S-(R*,R*))- (S-(R*,R*))-2,6-Diaminoheptanedioicacid (2S,6S)-2,6-diaminoheptanedioicacid (2S,6S)-(+)-2,6-diaminopimelicacid (2S,6S)-(+)-diaminopimelicacid (2S,6S)-2,6-diaminopimelicacid (S,S)-2,6-diaminopimelicacid L,L-2,6-diaminopimelicacid L,L-diaminopimelicacid LS-threo-2,6-diamino-heptanedioicacid

Molecular Formula: C7H14N2O4

Molecular Weight: 190.2

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

(2S,6S)-2,6-Diaminopimelic acid (DAP) is a non-proteinogenic diamino dicarboxylic acid. It is a key structural component of the peptidoglycan layer in the cell walls of most Gram-negative and some Gram-positive bacteria. The molecule contains two chiral centers, and the (2S,6S) stereoisomer is the biologically relevant form found in nature. Its primary significance lies in microbiology and immunology. DAP is an essential building block for bacterial cell wall synthesis, and its biosynthetic pathway is a target for antibiotic development. Furthermore, it is a potent activator of the NOD1 (nucleotide-binding oligomerization domain-containing protein 1) innate immune receptor in mammalian cells. This property makes it a crucial research tool for studying host-pathogen interactions, inflammation, and immune signaling pathways. Due to its unique structure featuring two amino and two carboxyl groups, it also serves as a chiral building block in organic synthesis and peptide chemistry. It is commonly used to prepare complex molecules and as a standard in analytical studies of bacterial cell wall composition.

Physical Properties

Boiling Point: 426.7 °C at 760 mmHg

Flash Point: 211.8 °C

Density: 1.344 g/cm3