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A0936

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

Name: N-Acetylmuramyl-Ala-<SC>D</SC>-isoglutaminyl-Nε-stearoyl-Lys
Brand: SIGMA

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

GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Effect of MDP-Lys(L18) as a mucosal immunoadjuvant on protection of mucosal infections by Sendai virus and rotavirus.

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

Induction of tumor necrosis factor-alpha in solid tumor region by the orally administered synthetic muramyl dipeptide analogue, romurtide.

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.

Alteration of spleen lymphocyte populations in rats with arthritis induced by muramyl dipeptide analogue or complete adjuvant.

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

Romurtide, a synthetic muramyl dipeptide derivative, promotes megakaryocytopoiesis through stimulation of cytokine production in nonhuman primates with myelosuppression.

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

Inflammatory cytokine production induced by an analogue of muramyl dipeptide MDP-Lys(L18) in rat macrophage cultures and dog synovial fluid.

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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