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D9904

Sigma-Aldrich

Nα,Nε-Diacetyl-Lys-D-Ala-D-Ala

carboxypeptidase substrate

Synonym(s):

(Ac)2-L-Lys-D-Ala-D-Ala

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About This Item

Empirical Formula (Hill Notation):
C16H28N4O6
CAS Number:
24570-39-6
Molecular Weight:
372.42
MDL number:
MFCD00037235
UNSPSC Code:
12352204
PubChem Substance ID:
24894333
NACRES:
NA.32

Quality Level

200

assay

≥98% (HPLC)

form

powder

composition

Peptide content, ≥85%

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

OC([C@@H](C)NC([C@@H](C)NC([C@@H](NC(C)=O)CCCCNC(C)=O)=O)=O)=O

InChI

1S/C16H28N4O6/c1-9(14(23)19-10(2)16(25)26)18-15(24)13(20-12(4)22)7-5-6-8-17-11(3)21/h9-10,13H,5-8H2,1-4H3,(H,17,21)(H,18,24)(H,19,23)(H,20,22)(H,25,26)

InChI key

VIHGYLJIMMKSBR-UHFFFAOYSA-N

Substrates

Substrate for penicillin-sensitive D-alanine carboxypeptidase.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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A Malabarba et al.
Journal of medicinal chemistry, 35(22), 4054-4060 (1992-10-30)
Basic carboxamides of teicoplanin A2 (CTA) and its aglycon (TD) are prepared by condensation of the 63-carboxyl function of these antibiotics with linear or branched polyamines. The antimicrobial activities of some of the resulting compounds were better than those of
Casey C McComas et al.
Journal of the American Chemical Society, 125(31), 9314-9315 (2003-08-02)
The binding affinity of 4, which incorporates a methylene (CH2) in place of the key linking amide of Ac2-l-Lys-d-Ala-d-Ala, for vancomycin was compared with that of Ac2-l-Lys-d-Ala-d-Ala (3) and Ac2-l-Lys-d-Ala-d-Lac (5). The vancomycin affinity for 4 was approximately 10-fold less
Cleidiane G Zampronio et al.
Analytical chemistry, 76(17), 5172-5179 (2004-09-18)
Electrospray ionization (ESI) is extensively used in the analysis of biological compounds; yet some fundamental properties of this technique are not completely understood. It is widely recognized that care should be exercised when noncovalent complexes are being studied by ESI
T R Herrin et al.
Journal of medicinal chemistry, 28(9), 1371-1375 (1985-09-01)
A series of ristocetin analogues with modifications (OH, C=O, C=NOH, NCOCH3) at the C-1' amino group was synthesized and found to possess antibacterial activity against gram-positive bacteria and to bind to Ac2-Lys-D-Ala-D-Ala, a model for the antibiotic's site of action.
M Nguyen-Distèche et al.
The Biochemical journal, 207(1), 109-115 (1982-10-01)
The membrane-bound, 26 000-Mr penicillin-binding protein of Streptomyces K15 has been isolated in the form of an effective, penicillin-sensitive D-alanyl-D-alanine-cleaving peptidase exhibiting high transpeptidase activity (greater than 95%) and very low carboxy-peptidase activity (less than 5%). The penicillin-binding protein/transpeptidase can
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