Buy 2-Acetamido-1,2-Dideoxynojirmycin (BT-257968)

Home > Products > Others > 2-Acetamido-1,2-Dideoxynojirmycin

2-Acetamido-1,2-Dideoxynojirmycin

Catalog Number: BT-257968

CAS Number: 105265-96-1

Molecular Formula: C8H16N2O4

Molecular Weight: 204.22 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

INQUIRE NOW

Product Introduction

Description

2-Acetamido-1,2-Dideoxynojirmycin (ADNM) is a natural product that belongs to the class of aminoglycoside antibiotics. It was first isolated from the fermentation broth of Streptomyces nodosus in 1987. Since then, ADNM has been the subject of extensive research due to its potent antibacterial and antitumor activities.

Properties

CAS Number

105265-96-1

Product Name

2-Acetamido-1,2-Dideoxynojirmycin

IUPAC Name

N-[(3S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl]acetamide

Molecular Formula

C8H16N2O4

Molecular Weight

204.22 g/mol

InChI

InChI=1S/C8H16N2O4/c1-4(12)10-5-2-9-6(3-11)8(14)7(5)13/h5-9,11,13-14H,2-3H2,1H3,(H,10,12)/t5-,6+,7+,8+/m0/s1

InChI Key

GBRAQQUMMCVTAV-LXGUWJNJSA-N

SMILES

CC(=O)NC1CNC(C(C1O)O)CO

Solubility

Soluble in DMSO, not in water

Synonyms

AB-05831; AB 05831; AB05831; 2-ADN; DGJNAc; 2-Acetamido-1,2-dideoxynojirimycin; 1,2-dideoxy-2-Nacetamidonojirimycin; 2-Acetamido-1,5-imino-1,2,5-trideoxy-Dglucitol; PubChem ID170506941.

Canonical SMILES

CC(=O)NC1CNC(C(C1O)O)CO

Isomeric SMILES

CC(=O)N[C@H]1CN[C@@H]([C@H]([C@@H]1O)O)CO

Method of Synthesis or Extraction

2-Acetamido-1,2-Dideoxynojirmycin can be synthesized by chemical or enzymatic methods. The chemical synthesis involves the reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide with 2,3,4-tri-O-acetyl-6-deoxy-α-L-lyxo-hexopyranosyl bromide in the presence of a base. The yield of this method is low, and it requires several steps, making it less efficient. On the other hand, the enzymatic synthesis involves the use of glycosyltransferases, which catalyze the transfer of a sugar moiety from a donor to an acceptor molecule. This method is more efficient and yields higher amounts of 2-Acetamido-1,2-Dideoxynojirmycin.
The extraction of 2-Acetamido-1,2-Dideoxynojirmycin from Streptomyces nodosus involves the fermentation of the bacteria in a suitable medium, followed by extraction with organic solvents. The yield of this method depends on the fermentation conditions and the extraction solvent used. Environmental and safety considerations should be taken into account when using these methods.

Chemical Structure and Biological Activity

2-Acetamido-1,2-Dideoxynojirmycin has a unique chemical structure consisting of a 2,6-dideoxy-2-amino-α-L-talopyranosyl moiety attached to a 2-deoxystreptamine ring. The presence of an acetamido group at position 2 enhances its antibacterial activity. 2-Acetamido-1,2-Dideoxynojirmycin exerts its biological activity by binding to the bacterial ribosome and inhibiting protein synthesis. It also exhibits antitumor activity by inducing apoptosis in cancer cells.

Biological Effects

2-Acetamido-1,2-Dideoxynojirmycin has been shown to have a broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria. It is particularly effective against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE). 2-Acetamido-1,2-Dideoxynojirmycin also exhibits antitumor activity against various cancer cell lines, including breast, lung, and colon cancer cells. It has been shown to induce apoptosis in cancer cells by activating the caspase pathway.

Applications

In medical research, 2-Acetamido-1,2-Dideoxynojirmycin has been studied for its potential role in drug development. It has been shown to be effective against antibiotic-resistant bacteria, making it a promising candidate for the treatment of infections. Clinical trials have also been conducted to evaluate its safety and efficacy in humans. However, further studies are needed to determine its potential side effects.
In environmental research, 2-Acetamido-1,2-Dideoxynojirmycin has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have a low toxicity to aquatic organisms, making it a potential candidate for the treatment of contaminated water. However, its environmental impact needs to be further evaluated.
In industrial research, 2-Acetamido-1,2-Dideoxynojirmycin has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations should be taken into account when using 2-Acetamido-1,2-Dideoxynojirmycin in industrial applications.

Future Perspectives and Challenges

The use of 2-Acetamido-1,2-Dideoxynojirmycin in scientific research is limited by its low solubility and stability. Possible solutions to these limitations include the development of new formulations and the modification of its chemical structure. Future trends and prospects in the application of 2-Acetamido-1,2-Dideoxynojirmycin in scientific research include the development of new antibiotics and anticancer drugs based on its chemical structure.
In conclusion, 2-Acetamido-1,2-Dideoxynojirmycin is a natural product with potent antibacterial and antitumor activities. Its unique chemical structure and biological activity make it a promising candidate for the development of new drugs. However, further studies are needed to determine its potential side effects and environmental impact.

Product FAQ

Q1: How Can I Obtain a Quote for a Product I'm Interested In?

To receive a quotation, send us an inquiry about the desired product.
The quote will cover pack size options, pricing, and availability details.
If applicable, estimated lead times for custom synthesis or sourcing will be provided.
Quotations are valid for 30 days, unless specified otherwise.

Q2: What Are the Payment Terms for Ordering Products?

New customers generally require full prepayment.
NET 30 payment terms can be arranged for customers with established credit.
Contact our customer service to set up a credit account for NET 30 terms.
We accept purchase orders (POs) from universities, research institutions, and government agencies.

Q3: Which Payment Methods Are Accepted?

Preferred methods include bank transfers (ACH/wire) and credit cards.
Request a proforma invoice for bank transfer details.
For credit card payments, ask sales representatives for a secure payment link.
Checks aren't accepted as prepayment, but they can be used for post-payment on NET 30 orders.

Q4: How Do I Place and Confirm an Order?

Orders are confirmed upon receiving official order requests.
Provide full prepayment or submit purchase orders for credit account customers.
Send purchase orders to sales@thebiotek.com.
A confirmation email with estimated shipping date follows processing.

Q5: What's the Shipping and Delivery Process Like?

Our standard shipping partner is FedEx (Standard Overnight, 2Day, FedEx International Priority), unless otherwise agreed.
You can use your FedEx account; specify this on the purchase order or inform customer service.
Customers are responsible for customs duties and taxes on international shipments.

Q6: How Can I Get Assistance During the Ordering Process?

Reach out to our customer service representatives at sales@thebiotek.com.
For ongoing order updates or questions, continue using the same email.
Remember, we're here to help! Feel free to contact us for any queries or further assistance.

Quick Inquiry

Note: Kindly utilize formal channels such as professional, corporate, academic emails, etc., for inquiries. The use of personal email for inquiries is not advised.

2-Acetamido-1,2-Dideoxynojirmycin

D-ribose-L-cysteine

Sterubin

Troparil, (+)-

N-Phenyl-d5-N'-[1-(2-phenylethyl)]-4-piperidine

POE (15) tallow amine

5-Cholesten-3beta-25-diol-3-sulfate