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A0936

Sigma-Aldrich

N-Acetylmuramyl-Ala-D-isoglutaminyl-Nε-stearoyl-Lys

Synonym(s):

MDP-LYS(L18), Muroctasin, Romurtide

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About This Item

Empirical Formula (Hill Notation):
C43H78N6O13
CAS Number:
78113-36-7
Molecular Weight:
887.11
MDL number:
MFCD00871261
UNSPSC Code:
12352200
PubChem Substance ID:
24890471

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCCCC(=O)NCCCC[C@H](NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O)C(N)=O)C(O)=O

InChI

1S/C43H78N6O13/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23-34(52)45-26-21-20-22-32(42(58)59)48-35(53)25-24-31(39(44)55)49-40(56)28(2)46-41(57)29(3)61-38-36(47-30(4)51)43(60)62-33(27-50)37(38)54/h28-29,31-33,36-38,43,50,54,60H,5-27H2,1-4H3,(H2,44,55)(H,45,52)(H,46,57)(H,47,51)(H,48,53)(H,49,56)(H,58,59)/t28-,29+,31+,32-,33+,36+,37+,38+,43?/m0/s1

InChI key

FKHUGQZRBPETJR-FZKCHLSLSA-N

Biochem/physiol Actions

MDP-LYS(L18), a synthetic analogue of MDP (muramyl dipeptide) derived from bacterial cell walls, is used as a potent immunoadjuvant that enhances protective immunity through activation of monocyte-macrophage lineage cells, such as dendritic cells.
N-Acetylmuramyl-Ala-D-isoglutaminyl-Nε-stearoyl-Lys, Romurtide, a muramyl dipeptide analogue, is a granulocyte-macrophage colony-stimulating factor and a TNF-α inducer.
Antibiotic peptide.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

A0936-250UG:
A0936-BULK:
A0936-1MG:
A0936-VAR:

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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A Fukushima et al.
Vaccine, 14(6), 485-491 (1996-04-01)
To examine the effect of MDP-Lys(L18), a derivative of muramyl dipeptide (MDP), as a mucosal immunoadjuvant, we investigated its activity to augment host resistance against mucosal infections by Sendai virus and rotavirus in mice. In an experimental infection model using
H Ueda et al.
International immunopharmacology, 1(1), 97-104 (2001-05-23)
The novel applications of a muramyl dipeptide analogue, romurtide, were investigated. When mice were intravenously injected with 10-1000 micrograms/mouse of romurtide as a primer and 3 KE/mouse of OK-432 as a trigger, systemic tumor necrosis factor-alpha (TNF-alpha) activity was increased.
T Sugawara et al.
International journal of tissue reactions, 17(1), 5-13 (1995-01-01)
To examine the involvement of lymphocytes in the development of MDP-Lys(L18)-induced arthritis (MIA) in rats and the exacerbation of MIA by cyclosporin A (CsA), we analysed the spleen lymphocyte subset using monoclonal antibodies and flow cytometry during the development of
K Namba et al.
Vaccine, 15(4), 405-413 (1997-03-01)
The response of megakaryocytes and cytokines to the administration of romurtide, a synthetic muramyl dipeptide derivative, was investigated in monkeys with myelosuppression by carboplatin-treatment. Romurtide increased the number of megakaryocytes and promoted the shift of megakaryocytes towards high ploidy class
T Sugawara et al.
Inflammation, 20(1), 43-56 (1996-02-01)
To examine the involvement of cytokines in the mechanisms of N2-[(N-acetylmuramoyl)-L-alanyl-D-isoglutaminyl]-N6-stearoyl-L-lysine, MDP-Lys(L18)-induced arthritis, we analyzed interleukin-1 (IL-1), tumor necrosis factor (TNF), colony-stimulating factor (CSF), and neutrophil chemotactic factor (NCF) by bioassays in the rat macrophage-conditioned medium (Mluminal diameter-CM) stimulated by
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