DAMME

DAMME is a stable synthetic analog of methionine enkephalin. Actions are similar to those of methionine enkephalin. It can be reversed by narcotic antagonists such as naloxone. It is one of the best-known analogs that has undergone fairly extensive clinical testing.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: 10-101-79

CAS No:64854-64-4 (net)

Synonyms/Alias:D-Ala(2); MePhe(4); Met(0)-ol-enkephalin; FK 33-824; FK-33-824; FK-33824; CID11758339; DL-tyrosyl-DL-alanyl-glycyl-N-methyl-DL-phenylalanyl-S-oxo-DL-methioninol;Tyr Ala Gly MePhe Met OH; Tyr-Ala-Gly-MePhe-Met-OH

Chemical Name:2-amino-N-[1-[[2-[[1-[(1-hydroxy-4-methylsulfinylbutan-2-yl)amino]-1-oxo-3-phenylpropan-2-yl]-methylamino]-2-oxoethyl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide

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M.F/Formula
C29H41N5O7S
M.W/Mr.
603.73
Sequence
One Letter Code: YAGFX
Three Letter Code: H-DL-Tyr-DL-Ala-Gly-DL-N(Me)Phe-DL-Met(O)-ol
Application
DAMME exerts a potent analgesic effect after systemic administration.
Areas of Interest
Analgesics

DAMME (Diaminomannitol Mannopyranoside Ester) is a specialized carbohydrate compound recognized for its unique structural features and versatile functionality in a variety of scientific research domains. Characterized by its diaminomannitol backbone and mannopyranoside ester moiety, DAMME offers a distinctive profile that facilitates its integration into complex biochemical systems. Its water solubility and compatibility with a wide range of solvents make it a valuable tool for both synthetic and analytical applications. Researchers often select this compound for its ability to participate in glycosylation reactions, as well as its potential to mimic or interfere with natural carbohydrate-protein interactions. The presence of multiple functional groups enables targeted chemical modifications, expanding its utility in custom synthesis and molecular engineering. As a result, DAMME has become a prominent choice in carbohydrate chemistry, glycobiology, and material science investigations.

Glycoconjugate Synthesis: In the field of glycoconjugate synthesis, DAMME serves as a reliable building block for the assembly of complex oligosaccharides and glycopeptides. Its diaminomannitol core allows for selective protection and deprotection strategies, facilitating the stepwise construction of carbohydrate chains. Researchers leverage its reactivity to create specific glycosidic linkages, which are crucial for studying molecular recognition processes and for the development of glycomimetic compounds. By incorporating this carbohydrate compound into synthetic pathways, scientists can efficiently generate libraries of structurally diverse glycoconjugates for subsequent biological evaluation and functional analysis.

Enzyme Substrate and Inhibitor Studies: As a structurally defined carbohydrate, DAMME is frequently employed in enzyme kinetics and inhibition assays, particularly those involving glycosidases and glycosyltransferases. Its esterified mannopyranoside unit can act as either a substrate analog or a competitive inhibitor, providing insights into enzyme specificity and catalytic mechanisms. Researchers utilize this compound to probe the active sites of carbohydrate-processing enzymes, enabling the elucidation of substrate recognition patterns and the identification of key catalytic residues. Such studies are instrumental in advancing the understanding of enzymatic pathways in both prokaryotic and eukaryotic systems.

Carbohydrate-Based Material Science: DAMME is increasingly applied in the design and fabrication of carbohydrate-based materials, such as hydrogels, nanocomposites, and polymeric scaffolds. Its multifunctional groups permit covalent attachment to various polymer backbones, enhancing the mechanical properties and bioactivity of the resulting materials. Scientists exploit its hydrophilicity and molecular flexibility to develop smart materials that respond to environmental stimuli or facilitate cell adhesion and proliferation. These carbohydrate-derived materials play a significant role in tissue engineering, drug delivery, and biosensor development, where tailored surface chemistry and biocompatibility are essential.

Lectin Binding and Glycan Array Development: The unique structure of DAMME makes it an ideal probe for lectin binding studies and glycan array construction. By immobilizing this compound on solid supports, researchers can systematically investigate carbohydrate-protein interactions, identify novel lectin ligands, and map binding specificities. Such applications are critical for deciphering the molecular basis of cell-cell communication, pathogen recognition, and immune response modulation. The ability to fine-tune the presentation and density of this carbohydrate on assay platforms allows for high-throughput screening and quantitative analysis of glycan-binding proteins.

Pathogen Interaction and Inhibition Research: DAMME is utilized in studies aimed at understanding and disrupting pathogen-host interactions mediated by carbohydrates. Its mannopyranoside ester moiety can mimic natural cell surface glycans, enabling researchers to investigate the mechanisms by which bacteria and viruses recognize and adhere to host tissues. By introducing this compound into model systems, scientists can evaluate its potential to block or alter pathogen binding, thereby providing valuable information for the development of anti-adhesive agents and the study of infection pathways.

In summary, DAMME stands out as a multifaceted carbohydrate compound with broad applicability across synthetic chemistry, enzymology, material science, glycomics, and pathogen research. Its versatile reactivity, structural adaptability, and compatibility with a range of experimental techniques make it an indispensable tool for advancing fundamental and applied carbohydrate research. Whether serving as a synthetic precursor, enzyme probe, material modifier, glycan array component, or pathogen interaction modulator, this compound continues to drive innovation and discovery in multiple scientific disciplines.

Source#
Synthetic
Solubility
?20°C
InChI
InChI=1S/C29H41N5O7S/c1-19(32-28(39)24(30)15-21-9-11-23(36)12-10-21)27(38)31-17-26(37)34(2)25(16-20-7-5-4-6-8-20)29(40)33-22(18-35)13-14-42(3)41/h4-12,19,22,24-25,35-36H,13-18,30H2,1-3H3,(H,31,38)(H,32,39)(H,33,40)
InChI Key
HYZHONGSQNXMPH-UHFFFAOYSA-N
Canonical SMILES
CC(C(=O)NCC(=O)N(C)C(CC1=CC=CC=C1)C(=O)NC(CCS(=O)C)CO)NC(=O)C(CC2=CC=C(C=C2)O)N
BoilingPoint
1033.4±65.0 °C at 760 mmHg
Melting Point
N/A

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