922-54-3 Usage
Description
(6R,2S)-Diaminopimelic acid, also known as meso-2,6-diaminopimelic acid, is a chiral amino acid that plays a crucial role in the biosynthesis of peptidoglycan, a major component of bacterial cell walls. It is characterized by its unique stereochemistry, with the R configuration at the 6th carbon and the S configuration at the 2nd carbon. This distinctive structure makes it an important molecule for understanding the mechanisms of bacterial cell wall synthesis and for developing new antimicrobial agents.
Uses
Used in Pharmaceutical Research:
(6R,2S)-Diaminopimelic acid is used as a research compound for studying the structure and function of peptidoglycan within the cell walls of bacteria. Its unique stereochemistry allows researchers to investigate the specific interactions and mechanisms involved in peptidoglycan synthesis, which is essential for bacterial growth and survival.
Used in Antibacterial Drug Development:
(6R,2S)-Diaminopimelic acid is used as a target for the development of new antibacterial drugs. By inhibiting the enzymes involved in the biosynthesis of this amino acid, researchers can disrupt the formation of peptidoglycan and ultimately inhibit bacterial growth. This approach has the potential to lead to the discovery of novel antibiotics that are effective against drug-resistant bacteria.
Used in Biochemical Education:
(6R,2S)-Diaminopimelic acid can be used as an educational tool in biochemical courses to teach students about the importance of stereochemistry in biological systems. By studying the structure and function of this amino acid, students can gain a deeper understanding of the molecular basis of bacterial cell wall synthesis and the potential for developing new antimicrobial agents.
Biochem/physiol Actions
Penultimate biosynthetic precursor of the essential amino acid L-lysine. Component of peptidoglycan in the cell wall of many bacteria.
Check Digit Verification of cas no
The CAS Registry Mumber 922-54-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 2 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 922-54:
(5*9)+(4*2)+(3*2)+(2*5)+(1*4)=73
73 % 10 = 3
So 922-54-3 is a valid CAS Registry Number.
922-54-3Relevant articles and documents
A simple chromatographic route for the isolation of meso diaminopimelic acid
Toth, Gabor K.,Hetenyi, Anasztazia,Ilisz, Istvan,Peter, Antal
experimental part, p. 133 - 137 (2011/11/05)
Meso diaminopimelic acid is an important noncoded amino acid found in Gram-negative bacterial peptidoglycan. In spite of its importance, this stereoisomer is not available commercially. A simple, economical procedure was developed for the isolation of pur
An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation
Wang,Xiong,Yang,Hruby
, p. 94 - 98 (2007/10/03)
An efficient synthesis of the title compounds 1 and 2 has been successfully developed. The key step is the asymmetric hydrogenation of dehydroamino acid 7 using [Rh(I)(COD)-(S,S) or - (R,R)-Et-DuPHOS)]+OTf- to produce the optically active, protected amino acid derivatives in high ee (>95%). The approach also can be used for the synthesis of other isomers and analogues.
A concise, stereoselective synthesis of meso-2,6-diaminopimelic acid (DAP)
Collier, Philip N.,Patel, Ian,Taylor, Richard J.K.
, p. 5953 - 5954 (2007/10/03)
The preparation of meso-2,6-diaminopimelic acid 1 is described. The key step in the synthesis is Suzuki coupling of the novel organoboron homoalanine equivalent 3 with methyl (2Z)-3-bromo-2-[(tert-butoxycarbonyl)amino]-2-propenoate 5.
