(2R)-2-[(2R)-2-aminopropanamido]propanoic acid

• ChemBase ID: 155487
• Molecular Formular: C6H12N2O3
• Molecular Mass: 160.17108
• Monoisotopic Mass: 160.08479225
• SMILES: C[C@H](C(=O)N[C@H](C)C(=O)O)N
• Canonical SMILES: C[C@H](C(=O)O)NC(=O)[C@H](N)C
• InChI: InChI=1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)/t3-,4-/m1/s1
• InChIKey: DEFJQIDDEAULHB-QWWZWVQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2R)-2-aminopropanamido]propanoic acid
• IUPAC Traditional name: D-ala-D-ala
• Synonyms: D-Ala-D-Ala

Database IDs

• CAS Number: 923-16-0
• MDL Number: MFCD00066038
• PubChem SID: 162249625; 24890468
• PubChem CID: 5460362

CALCULATED PROPERTIES

• Acid pKa: 3.7263415
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.3826344
• LogD (pH = 7.4): -3.4162068
• Log P: -3.3796766
• Molar Refractivity: 37.7947 cm^3
• Polarizability: 15.131784 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C6H12N2O3

DETAILS

Sigma Aldrich - A0912

Biochem/physiol Actions
D-Ala-D-Ala is found in the stem termini of peptidoglycan side-chain pentapeptide found in the cell walls of gram positive bacteria. The D-ala-d-ala stem termini is the site of interaction of glycopeptide antibiotics such as vancomycin and teicoplanin. D-ala-D-ala is a substrate used to study kinetics of UDPMurNAc-tripeptide D-alanyl-D-alanine-adding (ligase) enzyme.
D-Ala-D-Ala, a terminus moiety of bacterial peptidoglycans, is used for affinity chromatography and binding mechanism studies of antibiotics such as teicoplanin, ristocetin, vancomycin.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A0912.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.