Calichemicin gamma1

Base Information

• Chemical Name: Calichemicin gamma1
• CAS No.: 108212-75-5
• Molecular Formula: C₅₅H₇₄IN₃O₂₁S₄
• Molecular Weight: 1368.37
• European Community (EC) Number: 813-745-9

Synonyms:calicheamicin gamma(1)I;calichemicin gamma1

Chemical Property of Calichemicin gamma1

Chemical Property:

• Refractive Index: 1.662
• Boiling Point: °Cat760mmHg
• PKA: 7.13±0.60(Predicted)
• Flash Point: °C
• PSA: 409.64000
• Density: 1.57g/cm³
• LogP: 4.36950
• XLogP3: 2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 27
• Rotatable Bond Count: 24
• Exact Mass: 1367.27424
• Heavy Atom Count: 84
• Complexity: 2500

Purity/Quality:

99% ^*data from raw suppliers

Calicheamicin >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC1COC(CC1OC)OC2C(C(C(OC2OC3C#CC=CC#CC4(CC(=O)C(=C3C4=CCSSSC)NC(=O)OC)O)C)NOC5CC(C(C(O5)C)SC(=O)C6=C(C(=C(C(=C6OC)OC)OC7C(C(C(C(O7)C)O)OC)O)I)C)O)O
• Isomeric SMILES: CCNC1COC(CC1OC)OC2C(C(C(OC2O[C@H]3C#C/C=C\C#C[C@@]\4(CC(=O)C(=C3/C4=C\CSSSC)NC(=O)OC)O)C)NOC5CC(C(C(O5)C)SC(=O)C6=C(C(=C(C(=C6OC)OC)OC7C(C(C(C(O7)C)O)OC)O)I)C)O)O
• General Description: Calicheamicin gamma(1)I is a potent enediyne antibiotic known for its ability to bind and cleave DNA, with its oligosaccharide moiety playing a critical role in DNA recognition and specificity. The synthesis of its analogues, such as those replacing carbohydrate ring E with a basic chain E', has been explored to study DNA-drug interactions, though solubility challenges limited further characterization. These efforts highlight the importance of structural modifications in optimizing DNA-binding properties for potential therapeutic applications.

Technology Process of Calichemicin gamma1

There total 3 articles about Calichemicin gamma1 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

C70H84IN3O23S4 (144668-44-0) → calicheamicin γ1I (108212-75-5)

Guidance literature:

With diethylamine; In tetrahydrofuran; water; at 25 ℃; for 1.5h;

DOI:10.1021/ja00051a063

Reference yield:

C96H142IN3O26S4Si4 (158862-55-6) → calicheamicin γ1I (108212-75-5)

Guidance literature:

With camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; Yield given. Multistep reaction; 1.) THF, 25 deg C, 96 h, 2.) THF, 0 deg C, 15 min;

Reference yield:

C96H142IN3O26S4Si4 → calicheamicin γ1I (108212-75-5)

Guidance literature:

With camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; Yield given. Multistep reaction; 1.) THF, H₂O, 2.) THF;

DOI:10.1021/jo951560x

upstream raw materials:

C₇₀H₈₄IN₃O₂₃S₄

C₉₆H₁₄₂IN₃O₂₆S₄Si₄

Downstream raw materials:

C₁₀₈H₁₄₂I₂N₆O₄₂S₅

C₅₄H₇₄IN₃O₂₁S₂

triphenylphosphine sulfide

Triphenylphosphine oxide

Refernces

Synthesis of analogues of the calicheamicin γ₁(I) oligosaccharide as potential DNA ligands

10.1016/S0040-4039(98)02135-2

The research aimed to chemically synthesize two analogues of the calicheamicin oligosaccharide, which is crucial for drug-DNA interaction and the selectivity and specificity of DNA cleavage. The study focused on the roles of carbohydrate rings D and E, the aromatic ring-C, and the β-N-O glycosidic bond on DNA-drug recognition events. The researchers reported the total synthesis of oligosaccharides 1 and 2, which replaced carbohydrate ring E with a basic chain E', either with or without the rhamnopyranosyl unit D. Key chemicals used in the synthesis process included 2,2,2-trifluoroethanesulfonyl chloride, benzoyl chloride, trifluoroethanesulfonate ester, 1,4-dibromobutane, sodium hydride, ethylamine, Fmoc-protected amine, sodium borohydride, boron trifluoride, and various other reagents and solvents. The synthesized oligosaccharides showed some binding to double-stranded DNA, but solubility issues prevented a detailed study. The work was financially supported by the Ministère de l'Enseignement Supérieur et de la Recherche and involved collaboration with experts in the field.

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