81382-09-4

Basic information

• Product Name: 25-dihydrosaframycin A
• Synonyms: 25-dihydrosaframycin A;N-[(7-Cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-epimino-4H-isoquino[3,2-b][3]benzazocin-9-yl)methyl]-2-hydroxypropionamide;Saframycin AH1;Saframycin AH2;Saframycin AR1
• CAS NO: 81382-09-4
• Molecular Formula: C29H32N4O8
• Molecular Weight: 564.58638
• Mol File: 81382-09-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 869.6°C at 760 mmHg
• Flash Point: 479.7°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 2.65E-35mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 25-dihydrosaframycin A(CAS DataBase Reference)
• NIST Chemistry Reference: 25-dihydrosaframycin A(81382-09-4)
• EPA Substance Registry System: 25-dihydrosaframycin A(81382-09-4)

Safety Data

• Hazardous Substances Data: 81382-09-4(Hazardous Substances Data)

Usage

Source

Isolated from Streptomyces species

Classification

Belongs to the saframycin class of antibiotics

Activities

Antibacterial: Exhibits potent antibacterial activity
Antitumor: Demonstrates strong antitumor activity

Chemical Structure

Complex polycyclic system
Contains a unique bis(aminoethyl)pyrrole moiety

Biological Activities

Bacterial Inhibition: Inhibits growth of various bacterial strains, including multidrug-resistant pathogens
Anticancer: Induces apoptosis and suppresses proliferation of cancer cells

Potential

Promising candidate for new antibiotics and anticancer agents

Research Interest

Subject of investigation for further therapeutic development

InChI:InChI=1/C29H32N4O8/c1-11-23(35)14-8-17-22-21-15(24(36)12(2)28(41-6)26(21)38)7-16(32(22)4)18(9-30)33(17)19(10-31-29(39)13(3)34)20(14)25(37)27(11)40-5/h13,16-19,22,34H,7-8,10H2,1-6H3,(H,31,39)

Downstream Products

• 66082-27-7 Saframycin A 

Relevant articles and documents

Chemo-enzymatic Total Syntheses of Jorunnamycin A, Saframycin A, and N-Fmoc Saframycin Y3

The antitumor tetrahydroisoquinoline (THIQ) alkaloids share a common pentacyclic scaffold that is biosynthesized by nonribosomal peptide synthetases involving unique enzymatic Pictet-Spengler cyclizations. Herein we report concise and divergent chemo-enzymatic total syntheses of THIQ alkaloids by merging precise chemical synthesis with in vitro engineered biosynthesis. A recombinant enzyme SfmC responsible for the biosynthesis of saframycin A was adapted for the assembly of these natural products and their derivatives, by optimizing designer substrates compatible with SfmC through chemical synthesis. The appropriately functionalized pentacyclic skeleton were efficiently synthesized by streamlining the linkage between SfmC-catalyzed multistep enzymatic conversions and chemical manipulations of the intermediates to install aminonitrile and N-methyl groups. This approach allowed rapid access to the elaborated pentacyclic skeleton in a single day starting from two simple synthetic substrates without isolation of the intermediates. Further functional group manipulations allowed operationally simple and expeditious syntheses of jorunnamycin A, saframycin A, and N-Fmoc saframycin Y3 that could be versatile and common precursors for the artificial production of other antitumor THIQ alkaloids and their variants.