103782-08-7

Basic information

• Product Name: ALLOSAMIDIN
• Synonyms: ALLOSAMIDIN;.beta.-D-Allopyranoside, (3aR,4R,5R,6S,6aS)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-5-yl 2-(acetylamino)-4-O-2-(acetylamino)-2-deoxy-.beta.-D-allopyranosyl-2-deoxy-
• CAS NO: 103782-08-7
• Molecular Formula: C₂₅H₄₂N₄O₁₄
• Molecular Weight: 622.62
• Mol File: 103782-08-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.78g/cm³
• Refractive Index: 1.696
• PKA: 12.76±0.70(Predicted)
• CAS DataBase Reference: ALLOSAMIDIN(CAS DataBase Reference)
• NIST Chemistry Reference: ALLOSAMIDIN(103782-08-7)
• EPA Substance Registry System: ALLOSAMIDIN(103782-08-7)

Safety Data

• Hazardous Substances Data: 103782-08-7(Hazardous Substances Data)

Usage

Uses

Allosamidin is a chitinase inhibitor that is a signal molecule for chitinase production. It promotes atherosclerosis in hyperlipidemic mice. It is a glycoside antibiotic.

InChI:InChI=1/C25H42N4O14/c1-8(33)26-14-17(36)16(35)11(6-31)39-23(14)42-22-12(7-32)40-24(15(19(22)38)27-9(2)34)41-21-10(5-30)20-13(18(21)37)28-25(43-20)29(3)4/h10-24,30-32,35-38H,5-7H2,1-4H3,(H,26,33)(H,27,34)/t10-,11+,12+,13+,14+,15+,16+,17-,18+,19-,20-,21+,22+,23-,24-/m0/s1

Upstream product

• 114621-74-8 (3aS,4R,5R,6S,6aS)-4-Acetoxy-6-(acetoxymethyl)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-allopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-allopyranoside 
• 136773-88-1 (3aR,4R,5R,6S,6aS)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside 
• 1319720-24-5 C₂₉H₄₆N₄O₁₆ 
• 136773-80-3 Allyl 3-O-benzyl-4,6-O-benzylidene-2-<2-(benzyloxycarbonyl)benzamido>-2-deoxy-α-D-allopyranoside 
• 136845-45-9 Allyl 4,6-O-benzylidene-2-(2-carboxybenzamido)-2-deoxy-α-D-allopyranoside 
• 136773-78-9 Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(methanesulfonyl)-D-glucopyranoside 
• 136845-44-8 Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 
• 136773-79-0 Allyl 2-Amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 
• 136845-48-2 (3aR,4R,5R,6S,6aS)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranoside 
• 136773-85-8 3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose 
• 136800-69-6 (3aS,4R,5R,6S,6aS)-4-Acetoxy-6-<(benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside 

Downstream Products

• 103766-13-8 (+/-)-3aS,6aS-dihydro-5R,6S-dihydroxy-2-(dimethylamino)-4S-(hydroxymethyl)cyclopentano<4,3-d>oxazole 
• 4710-95-6 D-glucosamine hydrochloride 
• 115699-20-2 (1S,5R)-3-dimethylamino-6-exo-hydroxy-8-exo-hydroxymethyl-2-oxa-4-azabicyclo<3.3.0>oct-3-en-7-endo-yl 2-acetamido-2-deoxy-β-D-allopyranoside 

Related news

Chitinase inhibitor ALLOSAMIDIN (cas 103782-08-7) promotes chitinase production of Streptomyces generally07/17/2019

Allosamidin is a family 18 chitinase inhibitor produced by Streptomyces. In its producing strain, Streptomyces sp. AJ9463, allosamidin promotes production of the family 18 chitinase originated from chi65 in a chitin medium through the two-component regulatory system encoded by chi65R and chi65S,...detailed

Preparation of ALLOSAMIDIN (cas 103782-08-7) and demethylALLOSAMIDIN (cas 103782-08-7) photoaffinity probes and analysis of ALLOSAMIDIN (cas 103782-08-7)-binding proteins in asthmatic mice07/16/2019

Allosamidins, metabolites of Streptomyces with strong inhibitory activities toward family 18 chitinases, show a variety of biological activities in various organisms. We prepared photoaffinity and biotinylated probes of allosamidin and demethylallosamidin, the N-demethyl derivative that shows mu...detailed

Relevant articles and documents

Syntheses and activity of carbohydrate-containing chitinase inhibitors

The pseudo-Trisaccharide allosamidin 1 is a potent inhibitor of all family 18 chitinases, and it is confirmed to have insecticidal and antifungal activities. However, the synthesis of allosamidins is very difficult, and it is a challengeable subject. Allosamidins were synthesized in solid/liquid phase and total solid phase, respectively. Solid/liquid-phase method realizes the partial solid-phase synthesis of allosamidins. Total solid-phase method greatly simplifies the purification process. Moreover, it indicated that the inhibitory activity of N,N'-diacetyl-β-chitobiosylallosamizoline 9 against chitinase from Bombyx mori was a little weaker than that of allosamidin 1.

Solid-phase synthesis of allosamidin

The solid-phase synthesis of allosamidin is described. After the NHCbz trichloroacetimidate donors were synthesized, solid-phase synthesis was performed using the Wang resin as support. The target allosamidin was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively. Georg Thieme Verlag Stuttgart New York.

Syntheses of the Fungicide/Insecticide Allosamidin and a Structural Isomer

A synthesis of the naturally occurring inhibitor of chitin metabolism, allosamidin 1, involves, as the key step, condensation between the allosamizoline derivative 39, prepared following oxyamination of the cyclopentene 19, and the disaccharide glycosylating agent 54 which was synthesised from 2-acetamido-2-deoxy-D-glucose.The structural isomer 59 of allosamidin is also reported.Brief biological test results obtained using isomers 1 and 59 are recorded.