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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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 Leyh-Bouille et al.
The Biochemical journal, 235(1), 177-182 (1986-04-01)
The values of the kinetic parameters that govern the interactions between the Streptomyces K15 DD-peptidase and beta-lactam compounds were determined by measuring the inactivating effect that these compounds exert on the transpeptidase activity of the enzyme and, in the case
Zhibo Yang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(9), 2081-2090 (2009-01-22)
Charge matters! The charge state significantly influences the conformation and the binding energy between vancomycin antibiotic and bacterial cell-wall analogue peptides (see figure). Surface-induced dissociation (SID) studies provide a quantitative comparison between the stabilities of different charge states of the
M Nguyen-Distèche et al.
The Biochemical journal, 235(1), 167-176 (1986-04-01)
In water, the purified 26 000-Mr membrane-bound DD-peptidase of Streptomyces K15 hydrolyses the ester carbonyl donor Ac2-L-Lys-D-Ala-D-lactate (release of D-lactate) and the amide carbonyl donor Ac2-L-Lys-D-Ala-D-Ala (release of D-alanine) with accumulation of acyl- (Ac2-L-Lys-D-alanyl-)enzyme. Whereas hydrolysis of the ester substrate
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