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Merck
CN

A0910

Ala-D-γ-Glu-Lys-D-Ala-D-Ala

≥97% (HPLC)

Synonym(s):

Peptidoglycan pentapeptide

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About This Item

Empirical Formula (Hill Notation):
C20H36N6O8
CAS Number:
2614-55-3
Molecular Weight:
488.54
NACRES:
NA.26
PubChem Substance ID:
24890467
UNSPSC Code:
12352202
MDL number:
MFCD00133044

Key Documents

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Product Name

Ala-D-γ-Glu-Lys-D-Ala-D-Ala, ≥97% (HPLC)

InChI

1S/C20H36N6O8/c1-10(22)16(28)26-14(20(33)34)7-8-15(27)25-13(6-4-5-9-21)18(30)23-11(2)17(29)24-12(3)19(31)32/h10-14H,4-9,21-22H2,1-3H3,(H,23,30)(H,24,29)(H,25,27)(H,26,28)(H,31,32)(H,33,34)

SMILES string

CC(N)C(=O)NC(CCC(=O)NC(CCCCN)C(=O)NC(C)C(=O)NC(C)C(O)=O)C(O)=O

InChI key

MCIBYIIODNXVSL-UHFFFAOYSA-N

assay

≥97% (HPLC)

form

powder

color

white

storage temp.

−20°C

Quality Level

200

Related Categories

Application

Ala-D-γ-Glu-Lys-D-Ala-D-Ala is the pentapeptide tail of the peptidoglycan precursor UDPMurNAc-l-Ala-γ-d-Glu-l-Lys(Gly)(5)-d-Ala-d-Ala. Ala-D-γ-Glu-Lys-D-Ala-D-Ala is used to study the role of this peptide stem in peptidoglycan biosynthesis, degradation and function.

Biochem/physiol Actions

L-Ala-D-Glu-gamma-L-Lys-D-Ala-D-Ala, peptidoglycan pentapeptide, is the antigenic peptide determinant of peptidoglycan useful in studies of mechanisms of action of glycopeptide antibiotics.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

常规特殊物品
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Certificates of Analysis (COA)

Lot/Batch Number
0000353771
0000353771
0000259393
0000259393
SLCP9773

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B Heymer et al.
Journal of immunology (Baltimore, Md. : 1950), 117(1), 23-26 (1976-07-01)
A radioimmunoassay has been developed for the measurement of antibodies to peptidoglycan in human sera including patients with rheumatic fever and juvenile rheumatoid arthritis. The assay is based on the percentage of binding of the hapten 125I-L-Ala-gamma-d-Glu-L-Lys-D-Ala-D-Ala, the major peptide
Ahmed Bouhss et al.
The Journal of biological chemistry, 277(48), 45935-45941 (2002-09-27)
The enzymatic synthesis of the complete l-alanyl(1)-l-alanine(2) side chain of the peptidoglycan precursors of Enterococcus faecalis was obtained in vitro using purified enzymes. The pathway involved alanyl-tRNA synthetase and two ligases, BppA1 and BppA2, that specifically transfer alanine from Ala-tRNA
B Heymer et al.
Zeitschrift fur Immunitatsforschung, experimentelle und klinische Immunologie, 149(2-4), 168-178 (1975-07-01)
Staphylococcus epidermidis peptidoglycans solubilized by sonication or lysozyme digestion, and synthetic peptidoglycan analogs such as HSA-carboxymethyl-Gly-L-Ala-L-Ala-D-Ala-D-Ala (HSA-pentapeptide) or L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala (pentapeptide) have been labeled with 125I and tested for their applicability in the radioactive antigen binding assay. Use of radioiodinated Staph.
Lorena Abadía Patiño et al.
Antimicrobial agents and chemotherapy, 49(4), 1419-1425 (2005-03-29)
Enterococcus faecalis BM4405-1, a susceptible derivative of the VanE-type vancomycin-resistant E. faecalis strain BM4405, was obtained after growth in the presence of novobiocin, an inhibitor of the GyrB subunit of DNA gyrase. In contrast to findings for BM4405, UDP-MurNAc-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala (pentapeptide[D-Ala])
G Folena-Wasserman et al.
Journal of chromatography, 392, 225-238 (1987-04-17)
An affinity support was designed to facilitate the isolation and purification of glycopeptide antibiotics by mimicking their known affinity for the bacterial cell wall. Members of this class of antibiotics inhibit peptidoglycan biosynthesis by specifically binding to pentapeptide precursors terminating
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