583-93-7 Usage
Description
2,6-Diaminopimelic acid (2,6-DAP) is an amino dicarboxylic acid that is heptanedioic acid with amino substituents at C-2 and C-6. It is produced in bacteria and is a component of the bacterial cell wall. Additionally, it is synthesized by higher plants and is used as a building block in the synthesis of various compounds.
Uses
Used in Bacterial Cell Wall Composition:
2,6-Diaminopimelic acid is used as a constituent of bacterial cell walls, playing a crucial role in the structural integrity and function of these organisms.
Used in Higher Plant Synthesis:
2,6-Diaminopimelic acid is used as a component in the synthesis of higher plants, contributing to their growth and development.
Used in Proteoglycan Synthesis:
2,6-Diaminopimelic acid is used as a constituent of proteoglycans, which are essential for various biological processes, including cell signaling, cell adhesion, and structural support.
Used in Pharmaceutical Industry:
2,6-Diaminopimelic acid (2,6-DAP) is used as a building block in the synthesis of tripeptides and γ-glutamyldiaminopimelic acid derivatives, which have potential applications in the development of new drugs and therapeutic agents.
Chemical Properties:
2,6-Diaminopimelic acid is a white to beige powder and/or chunks, which can be used in various applications due to its unique chemical structure and properties.
Biochem/physiol Actions
2,6-Diaminopimelic acid is essential for microbial metabolism and is a potential marker for quantification of microbial proteins. It is a sensitive and reliable marker and is majorly quantified using gradient high-performance liquid chromatography (HPLC).
Purification Methods
Crystallise the acid from H2O or aqueous EtOH. Also purify it by dissolving it in hot H2O and adding 5volumes of EtOH, filter after 12hours at -10o. The acid has been recrystallised from 35% aqueous EtOH [Wade et al. J Am Chem Soc 79 648, 651 1957]. [Beilstein 4 IV 3081.]
Check Digit Verification of cas no
The CAS Registry Mumber 583-93-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 3 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 583-93:
(5*5)+(4*8)+(3*3)+(2*9)+(1*3)=87
87 % 10 = 7
So 583-93-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m1/s1
583-93-7Relevant 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.
