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Merck
CN

05260

L-丙氨酰基-L-1-氨基乙基膦酸

≥95% (HPLC)

别名:

(S)-Alanyl-(R)-1-aminoethylphosphonic acid, Alafosfalin, Alaphosphin

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关于此项目

经验公式(希尔记法):
C5H13N2O4P
化学文摘社编号:
分子量:
196.14
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
EC Number:
262-362-8
Beilstein/REAXYS Number:
4801790
MDL number:
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assay

≥95% (HPLC)

form

powder

optical activity

[α]20/D −45±2°, c = 1% in H2O

color

white

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

cell wall synthesis | interferes, enzyme | inhibits

storage temp.

2-8°C

SMILES string

C[C@H](N)C(=O)N[C@@H](C)P(O)(O)=O

InChI

1S/C5H13N2O4P/c1-3(6)5(8)7-4(2)12(9,10)11/h3-4H,6H2,1-2H3,(H,7,8)(H2,9,10,11)/t3-,4+/m0/s1

InChI key

BHAYDBSYOBONRV-IUYQGCFVSA-N

General description

Chemical structure: amino acid derivatives

Application

Alaphosphin is used as a selection agent for isolation of Salmonella and as a dipeptide mimetic antibacterial agent.

Biochem/physiol Actions

Alaphosphin is an antibacterial phosphonopeptide which mimics the terminal dipeptide moiety (D-Ala-D-Ala) of bacterial cell wall peptidoglycan . It metabolizes aminophosphonic acid which inhibits alanine racemase and uridine 5-diphosphate-N-acetylmuramoylalanine synthetase.
Alaphosphin is used as a selection agent for isolation of Salmonella and as a dipeptide mimetic antibacterial agent. It metabolizes aminophosphonic acid which inhibits alanine racemase and uridine 5-diphosphate-N-acetylmuramoylalanine synthetase.

Packaging

250MG

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Store under inert gas. Moisture sensitive. Keep in a dry place.


pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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F R Atherton et al.
Antimicrobial agents and chemotherapy, 15(5), 696-705 (1979-05-01)
The novel antibacterial peptide mimetic alaphosphin (l-alanyl-l-1-aminoethylphosphonic acid) selectively inhibited peptidoglycan biosynthesis in both gram-negative and gram-positive bacteria. It induced accumulation of uridine diphosphate-N-acetyl-muramyl-tripeptide in gram-positive organisms and significantly reduced the intracellular pool levels of d-alanine. Alaphosphin was actively transported
K J Towner et al.
Bulletin of the World Health Organization, 58(5), 747-751 (1980-01-01)
Isolates of Vibrio cholerae obtained immediately after the outbreak of the fourth recorded epidemic of cholera in the United Republic of Tanzania were sensitive to tetracycline, but after five months of its extensive therapeutic and prophylactic use, 76% of the
M Arisawa et al.
Antimicrobial agents and chemotherapy, 21(5), 706-710 (1982-05-01)
Potentiating activity of alafosfalin was examined in detail with 8 cephalosporins and mecillinam against 164 urinary bacteria representing 8 genera. Alafosfalin was generally comparable in activity to cefamandole and mecillinam but superior to other cephalosporins tested. When the minimal fractional



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