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A0910

Sigma-Aldrich

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
MDL number:
MFCD00133044
UNSPSC Code:
12352202
PubChem Substance ID:
24890467
NACRES:
NA.26

Quality Level

200

Assay

≥97% (HPLC)

form

powder

color

white

storage temp.

−20°C

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

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)

InChI key

MCIBYIIODNXVSL-UHFFFAOYSA-N

Related Categories

Amino Acid Sequence

Ala-Glu-Lys-Ala-Ala

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 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)

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M Nieto et al.
The Biochemical journal, 123(5), 789-803 (1971-08-01)
Vancomycin forms complexes with peptides terminating in d-alanyl-d-alanine that are analogous to the biosynthetic precursors of bacterial mucopeptides. The specificity of complex-formation has been studied by means of many synthetic peptides, prepared by both solid-phase and conventional methods. The following
Immunochemistry of a synthetic peptidoglycan-precursor pentapeptide.
A R Zeiger et al.
Biochemistry, 12(18), 3387-3394 (1973-08-28)
V A Bokisch et al.
The Journal of experimental medicine, 138(5), 1184-1193 (1973-11-01)
The relationship between 7S anti-IgG and antibodies to streptococcal cell wall peptidoglycan was examined for four streptococcal Group C antisera. Homogeneous 7S anti-IgG components in these sera were isolated by means of an IgG immunoadsorbent column. For two of the
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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