73201-25-9

Upstream product

• 611180-79-1 C₆₅H₅₉N₇O₂₁ 
• 73412-13-2 φ-aglycoristocetin 

Downstream Products

• 1416228-08-4 C₇₄H₅₉N₇O₁₉S 
• 1416228-16-4 C₇₈H₆₁N₇O₁₉S 
• 66057-59-8 (2R,2'S)-actinoidinic acid 
• 54750-25-3 ristomycinic acid 
• 80243-65-8 2-Amino-3-{4-[5-(amino-carboxy-methyl)-2,3-dihydroxy-phenoxy]-phenyl}-propionic acid 

Relevant academic research and scientific papers

Click reaction synthesis of carbohydrate derivatives from ristocetin aglycon with antibacterial and antiviral activity

New sugar derivatives of ristocetin were prepared by copper-catalyzed 1,3-dipolar cycloaddition reaction using azido-ristocetin aglycon and various propargyl glycosides. Some of them were found to be active against Gram-positive bacteria and showed favorable antiviral activity against the H1N1 subtype of influenza A virus.

Preparation of Biologically Active Ristocetin Derivatives: Replacements of the 1'-Amino Group

A series of ristocetin analogues with modifications (OH, C=O, C=NOH, NCOCH3) at the C-1' amino group was synthesized and found to possess antibacterial activity against gram-positive bacteria and to bind to Ac2-Lys-D-Ala-D-Ala, a model for the antibiotic's site of action.Due to the lack of a positively charged amino group, the active analogues could not form a salt bridge, indicating that an electrostatic interaction between the positively charged 1'-amino group of ristocetin and the carboxylate anion of the peptide is not required for complex formation.The only compound that did not exhibit good antibacterial activity was epiristocetin aglycone (an analogue with the 1'-amino group in the opposite configuration (S) as ristocetin).On the basis of NMR studies of epiristocetin aglycone in solution, the 1'-amino group is located in the proposed carboxylate binding pocket and may sterically block complex formation.

Synthesis of fluorescent ristocetin aglycon derivatives with remarkable antibacterial and antiviral activities

Isoindole and benzoisoindole derivatives of ristocetin aglycon have been prepared by reaction with o-phthalaldehyde or naphthalene-2,3-dialdehyde and various thiols. The new compounds exhibited potent antibacterial and anti-influenza virus activity. The c

Diazo transfer-click reaction route to new, lipophilic teicoplanin and ristocetin aglycon derivatives with high antibacterial and anti-influenza virus activity: An aggregation and receptor binding study

Semisynthetic, lipophilic ristocetin and teicoplanin derivatives were prepared starting from ristocetin aglycon and teicoplanin ψ-aglycon (N-acetyl-D-glucosaminyl aglycoteicoplanin). The terminal amino functions of the aglycons were converted into azido f

Total Synthesis of the Ristocetin Aglycon

The first total synthesis of the ristocetin aglycon is described employing a modular and highly convergent strategy. An effective 12-step (12% overall) synthesis of the ABCD ring system 3 from its amino acid subunits sequentially features an intramolecular aromatic nucleophilic substitution reaction for formation of the diaryl ether and closure of the 16-membered CD ring system (65%), a respectively diastereoselective (3:1, 86%) Suzuki coupling for installation of the AB biaryl linkage on which the atropisomer stereochemistry can be further thermally adjusted, and an effective macrolactamization (51%) for closure of the 12-membered AB ring system. A similarly effective 13-step (14% overall) synthesis of the 14-membered EFG ring system 4 was implemented employing a room-temperature intermolecular SNAr reaction of an o-fluoronitroaromatic for formation of the FG diaryl ether (69%) and a key macrolactamization (92%) with formation of the amide linking residues 1 and 2. The two key fragments 3 and 4 were coupled, and the remaining 16-membered DE ring system was closed via diaryl ether formation to provide the ristocetin tetracyclic ring system (15 steps, 8% overall) enlisting an unusually facile (25 °C, 8 h, DMF, ≥95%) and diastereoselective (≥15:1) aromatic nucleophilic substitution reaction that benefits from substrate preorganization.

A new and improved method for deglycosidation of glycopeptide antibiotics exemplified with vancomycin, ristocetin, and ramoplanin

A general method for the deglycosidation of glycopeptide antibiotics has been developed. Treatment of vancomycin, ristocetin, and ramoplanin with anhydrous HF results in efficient cleavage of the sugars to provide the corresponding aglycons in high yield.