N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE

Basic Information

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CAS Number

53678-77-6

Molecular Formula

C19H32N4O11

Molecular Weight

492.48 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Boiling Point

1023.7°Cat760mmHg

Density

1.45

Flash Point

572.9°C

Solubility

H2O: 10 mg/mL, clear, colorless

Refractive Index

1.578

Specific Rotation

D25 +44° (acetic acid)

SMILES

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CC(C(=O)NC(CCC(=O)O)C(=O)N)NC(=O)C(C)OC1C(C(OC(C1O)CO)O)NC(=O)C

InChI

InChI=1S/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)/t7-,8+,10+,11+,13+,14+,15+,19?/m0/s1

InChIKey

BSOQXXWZTUDTEL-QAQREVAFSA-N

LogP

-4.325199999999993

Topological Polar Surface Area

246.83999999999997 Å²

Hydrogen Bond Donor/Acceptor

9 / 15

Complexity

765

Synonyms & References

English

s9709
53678-77-6
A937210
AS-64347
Adjuvant Peptide
(4R)-4-[[(2S)-2-[[(2R)-2-[(2S,3R,4R,5S,6R)-3-Acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
(4R)-4-((2S)-2-((2R)-2-((3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)propanamido)propanamido)-5-amino-5-oxopentanoic acid
Q259464
CHEMBL1779325
4-(TRIFLUOROACETYL)BENZOICACIDCHLORIDE
SCHEMBL41813
N-Acetylmuramoyl-L-alanyl-D-?-glutamine
Muramyl Dipeptide
MFCD00077638
NS00057787
D-a-Glutamine,N-(N-acetylmuramoyl)-L-alanyl-
(4R)-4-[[(2S)-2-[[(2R)-2-[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
N-Acetylmuramyl-L-alanyl-D-isoglutamine hydrate, >=98% (TLC)
(4R)-4-carbamoyl-4-[(2S)-2-[(2R)-2-{[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanoic acid
BDBM50505203
AKOS034831580
Ac-muramyl-Ala-D-Glu-NH?
Ac-muramyl-Ala-D-Glu-NH₂
Ac-muramyl-Ala-D-Isogln-OH, MDP, Muramyl Dipeptide
ADJUVANT PEPTIDE
N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE
: N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE
AC-MURAMYL-ALA-D-GLN
AC-MURAMYL-ALA-D-ISOGLN-OH
Adjuvant Peptide,Muramyl dipeptide
L-18-MDP

MDL Number

MFCD09842822

FAQ

What are the physical and chemical properties of N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE (CAS: 53678-77-6)?

N-AcetylMuramyl-L-Alanyl-D-Isoglutamine (CAS: 53678-77-6) is a crystalline compound with a molecular weight of approximately 457.4 g/mol. It has limited solubility in water and is practically insoluble in organic solvents. This compound is known to be highly reactive, particularly with nucleophiles and bases. It is susceptible to hydrolysis under basic conditions.

How is N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE (CAS: 53678-77-6) typically synthesized?

N-AcetylMuramyl-L-Alanyl-D-Isoglutamine (CAS: 53678-77-6) is typically synthesized through a multi-step process involving peptide coupling reactions. Key steps include the formation of the peptide bond between N-acetyl muramine and L-alanine, followed by the coupling with D-isoglutamine. The synthesis often employs coupling reagents like 1-hydroxybenzotriazole (HOBt) and N,N′-carbonyldiimidazole (CDI) with appropriate catalysis to enhance selectivity and yield.

What industries use N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE (CAS: 53678-77-6)?

N-AcetylMuramyl-L-Alanyl-D-Isoglutamine (CAS: 53678-77-6) is primarily used in the pharmaceutical industry, particularly in the development of vaccines and adjuvants. It also finds applications in the polymer industry for functionalization of polymer surfaces and in sensors for detection of specific biological molecules.

What precautions should be taken when handling N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE (CAS: 53678-77-6)?

When handling N-AcetylMuramyl-L-Alanyl-D-Isoglutamine (CAS: 53678-77-6), it is essential to wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or a fume hood to minimize inhalation risks. Spills should be immediately contained and cleaned up with appropriate absorbents. Refer to the Safety Data Sheet (SDS) for detailed safety information and emergency procedures.