95058-85-8

Basic information

• Product Name: α-Gemcitabine
• Synonyms: 2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2,2-difluoro-Alpha-D-erythro-pentofuranosyl)-
• CAS NO: 95058-85-8
• Molecular Formula: C₉H₁₁F₂N₃O₄
• Molecular Weight: 263.200846
• Mol File: 95058-85-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: α-Gemcitabine(CAS DataBase Reference)
• NIST Chemistry Reference: α-Gemcitabine(95058-85-8)
• EPA Substance Registry System: α-Gemcitabine(95058-85-8)

Safety Data

• Hazardous Substances Data: 95058-85-8(Hazardous Substances Data)

Usage

General Description

α-Gemcitabine is a modified form of the chemotherapy drug gemcitabine, designed to improve its effectiveness in treating cancer. It is a nucleoside analogue that inhibits the synthesis of DNA, leading to the death of rapidly dividing cancer cells. α-Gemcitabine has been shown to have greater stability and reduced side effects compared to gemcitabine, making it a promising option for cancer treatment. It is currently being researched and developed for clinical use in the treatment of various types of cancer, including pancreatic, breast, and lung cancer. Overall, α-Gemcitabine holds potential as a more effective and tolerable chemotherapy option for cancer patients.

Upstream product

• 1155863-81-2 C₂₃H₁₉F₂N₃O₆ 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 1173700-23-6 (3S,4R,5R)-3-fluoro-4-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)-dihydrofuran-2(3H)-one 
• 1173700-25-8 2-deoxy-2,2-difluoro-3,5-di-O-(triisopropylsilyl)-γ-D-ribonolactone 
• 1260238-57-0 2'-deoxy-2',2'-difluoro-3',5'-di-O-(triisopropylsilyl)cytidine 
• 1173700-36-1 1-methylsulfonyl-2-deoxy-2,2-difluoro-3,5-di-O-(triisopropylsilyl)-D-ribofuranose 
• 861445-90-1 C₁₃H₁₅F₂N₃O₆ 
• 952408-92-3 1-[2'-deoxy-2',2'-difluoro-3',5'-bis(tert-butyldiphenylsilyloxy)-ribofuranosyl]-cytosine 
• 18027-23-1 bis(trimethylsilyl)-N-acetylcytosine 
• 103882-89-9 3,5-bis-O-(tert-butyldimethylsilyl)-1-O-(methanesulfonyl)-2-deoxy-2,2-difluororibose 
• 122111-03-9 gemcitabine hydrochloride 

Relevant articles and documents

A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

Inactivation of lactobacillus leichmannii ribonucleotide reductase by 2',2'-difluoro2'-deoxycytidine s'-triphosphate: Covalent modification

Ribonucleotide reductase (RNR) from Lactobacillus leichmannii, a 76 kDa monomer using adenosylcobalamin (AdoCbl) as a cofactor, catalyzes the conversion of nucleoside triphosphates to deoxynucleotides and is rapidly ( 3H]- and [5-3H]F2CTP were synthesized and used independently to inactivate RNR. Sephadex G-50 chromatography of the inactivation mixture revealed that 0.47 equiv of a sugar was covalently bound to RNR and that 0.71 equiv of cytosine was released. Alternatively, analysis of the inactivated RNR by SDS-PAGE without boiling resulted in 33% of RNR migrating as a 110 kDa protein. Inactivation of RNR with a mixture of [1'-3H]F2CTP and [1'-2H]F 2CTP followed by reduction with NaBH4, alkylation with iodoacetamide, trypsin digestion, and HPLC separation of the resulting peptides allowed isolation and identification by MALDI-TOF mass spectrometry (MS) of a 3H/2H-labeled peptide containing C731 and C736 from the C-terminus of RNR accounting for 10% of the labeled protein. The MS analysis also revealed that the two cysteines were cross-linked to a furanone species derived from the sugar of F2CTP. Incubation of [1-3H]F2CTP with C119S-RNR resulted in 0.3 equiv of sugar being covalently bound to the protein, and incubation with NaBH4 subsequent to inactivation resulted in trapping of 2'-fluoro-2'-deoxycytidine. These studies and the ones in the preceding paper (DOI: 10.1021/bi9021318) allow proposal of a mechanism of inactivation of RNR by F2CTP involving multiple reaction pathways. The proposed mechanisms share many common features with F2CDP inactivation of the class I RNRs.

PREPARATION OF GEMCITABINE

A process for preparation of gemcitabine hydrochloride and purification thereof.