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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 420110789
| Watchedfields = changed
⚫ |ImageFile=Diaminopimelic acid.png
⚫ | verifiedrevid = 460781251
|ImageSize=200px
⚫ | ImageFile = Diaminopimelic acid.svg
|ImageFile2=Diaminopimelic_acid.gif | ImageFile2 = Diaminopimelic_acid.gif
|IUPACName=(2''R'',6''S'')-2,6-Diaminoheptanedioic acid | PIN = (2''R'',6''S'')-2,6-Diaminoheptanedioic acid
|OtherNames= | OtherNames =
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| IUPHAR_ligand = 5021
⚫ | CASNo=583-93-7
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | ChEMBL = 415306
⚫ | CASNo=583-93-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V5KRL7N7GD
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 415306
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16488 | ChEBI = 16488
| PubChem = 1549101 | PubChem = 1549101
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 89700 | ChemSpiderID = 89700
| SMILES = O=C(O)(N)CCC(N)C(=O)O | SMILES = O=C(O)(N)CCC(N)C(=O)O
| 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+
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | InChIKey = GMKMEZVLHJARHF-SYDPRGILBU
| StdInChI = 1S/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+ | StdInChI = 1S/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+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GMKMEZVLHJARHF-SYDPRGILSA-N
⚫ | StdInChIKey = GMKMEZVLHJARHF-SYDPRGILSA-N
| MeSHName=Diaminopimelic+acid | MeSHName = Diaminopimelic+acid
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C=7|H=14|N=2|O=4 | C=7 | H=14 | N=2 | O=4
| MolarMass=190.20 g/mol | MolarMass=190.20 g/mol
| Appearance= | Appearance= white powder
| Density= | Density=1.344 g/mL
| MeltingPtC= 295
| MeltingPt=
| BoilingPtC= 426.7
| BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards= Irritant
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''Diaminopimelic acid''' (DAP) is an ], representing an epsilon-carboxy derivative of ].


{{Distinguish|2,3-Diaminopropionic acid}}
⚫ DAP is a characteristic of certain ]s<ref name="isbn0-07-147666-0">{{cite book |author=Brooks, George H.; Geo F. Brooks |title=Jawetz, Melnick & Adelberg's medical microbiology |publisher=McGraw-Hill Medical |location= |year=2007 |pages=85 |isbn=0-07-147666-0 |oclc= |doi= |accessdate=}}</ref> of some bacteria. When provided, they exhibit normal growth. When in deficiency, they still grow but with the inability to make new cell wall proteoglycan.


'''Diaminopimelic acid''' ('''DAP''') is an ], representing an ]-] derivative of ]. ''meso''-α,ε-Diaminopimelic acid is the last intermediate in the biosynthesis of lysine and undergoes ] by ] to give the final product.<ref>{{Cite book |last=Voet |first=Donald |url=https://www.worldcat.org/title/690489261 |title=Biochemistry |last2=Voet |first2=Judith G. |date=2011 |publisher=John Wiley & Sons |isbn=978-0-470-57095-1 |edition=4th |location=Hoboken, NJ |pages=1072{{--}}1075 |oclc=690489261}}</ref>
⚫ This is also the attachment point for ].<ref>Seltmann, Guntram; Otto Holst (2002). ''The Bacterial Cell Wall.'' Springer, pp. 81-82.</ref>

⚫ DAP is a characteristic of certain ]s<ref name="isbn0-07-147666-0">{{cite book |author1=Brooks, George H. |author2=Geo F. Brooks |title=Jawetz, Melnick & Adelberg's medical microbiology |url=https://archive.org/details/jawetzmelnickade00broo_450 |url-access=limited |publisher=McGraw-Hill Medical |year=2007 |pages= |isbn=978-0-07-147666-9 }}</ref> of some bacteria. DAP is often found in the peptide linkages of ]-] chains that make up the cell wall of ] bacteria. When provided, they exhibit normal growth. When in deficiency, they still grow but with the inability to make new cell wall peptidoglycan.

⚫ This is also the attachment point for ].<ref>{{cite book |last=Seltmann |first=Guntram |first2=Otto |last2=Holst |year=2002 |title=The Bacterial Cell Wall |location=Berlin |publisher=Springer |pages=81–82 |isbn=3-540-42608-6 }}</ref>


==See also== ==See also==
* ], an enzyme involved in DAP synthesis
* ] * ]
* ] * ]
* ]


==Images== ==Images==
] ]


==References== ==References==
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{{Bacteria}} {{Bacteria}}


] ]
] ]
]




{{organic-compound-stub}} {{organic-compound-stub}}

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]
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Latest revision as of 14:43, 1 October 2024

Diaminopimelic acid
Names
Preferred IUPAC name (2R,6S)-2,6-Diaminoheptanedioic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.660 Edit this at Wikidata
IUPHAR/BPS
MeSH Diaminopimelic+acid
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/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+Key: GMKMEZVLHJARHF-SYDPRGILSA-N
SMILES
  • O=C(O)(N)CCC(N)C(=O)O
Properties
Chemical formula C7H14N2O4
Molar mass 190.20 g/mol
Appearance white powder
Density 1.344 g/mL
Melting point 295 °C (563 °F; 568 K)
Boiling point 426.7 °C (800.1 °F; 699.8 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound Not to be confused with 2,3-Diaminopropionic acid.

Diaminopimelic acid (DAP) is an amino acid, representing an epsilon-carboxy derivative of lysine. meso-α,ε-Diaminopimelic acid is the last intermediate in the biosynthesis of lysine and undergoes decarboxylation by diaminopimelate decarboxylase to give the final product.

DAP is a characteristic of certain cell walls of some bacteria. DAP is often found in the peptide linkages of NAM-NAG chains that make up the cell wall of gram-negative bacteria. When provided, they exhibit normal growth. When in deficiency, they still grow but with the inability to make new cell wall peptidoglycan.

This is also the attachment point for Braun's lipoprotein.

See also

Images

An alternate view of the DAP structure.

References

  1. Voet, Donald; Voet, Judith G. (2011). Biochemistry (4th ed.). Hoboken, NJ: John Wiley & Sons. pp. 1072–1075. ISBN 978-0-470-57095-1. OCLC 690489261.
  2. Brooks, George H.; Geo F. Brooks (2007). Jawetz, Melnick & Adelberg's medical microbiology. McGraw-Hill Medical. pp. 85. ISBN 978-0-07-147666-9.
  3. Seltmann, Guntram; Holst, Otto (2002). The Bacterial Cell Wall. Berlin: Springer. pp. 81–82. ISBN 3-540-42608-6.
Microbiology: Bacteria
Medical
microbiology
Biochemistry
and ecology
Oxygen
preference
Other
Shape
Structure
Cell
envelope
Outside
envelope
Composite
Taxonomy
and evolution


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