168264-15-1

Basic information

• Product Name: (2S,4S)-4-N³benzoylthymidyl-Boc-prolyl methyl ester
• Synonyms: (2S,4S)-4-N³benzoylthymidyl-Boc-prolyl methyl ester
• CAS NO: 168264-15-1
• Molecular Weight: 457.483
• Mol File: 168264-15-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,4S)-4-N³benzoylthymidyl-Boc-prolyl methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-4-N³benzoylthymidyl-Boc-prolyl methyl ester(168264-15-1)
• EPA Substance Registry System: (2S,4S)-4-N³benzoylthymidyl-Boc-prolyl methyl ester(168264-15-1)

Safety Data

• Hazardous Substances Data: 168264-15-1(Hazardous Substances Data)

Upstream product

• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 4330-20-5 N-3-benzoylthymine 
• 51-35-4 4R-4-hydroxyproline 
• 84520-67-2 (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 168264-31-1 (2S,4S)-2-(Benzyloxycarbonylmethyl-carbamoyl)-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Dideoxy nucleoside triphosphate (ddNTP) analogues: Synthesis and polymerase substrate activities of pyrrolidinyl nucleoside triphosphates (prNTPs)

The dideoxynucleoside triphosphates (ddNTPs) terminate the bio-polymerization of DNA and become essential chemical component of DNA sequencing technology which is now basic tool for molecular biology research. In this method the radiolabeled or fluorescent dye labeled ddNTP analogues are being used for DNA sequencing by detection of the terminated DNA fragment after single labeled ddNTP incorporation into DNA under PCR conditions. This report describes the syntheses of rationally designed novel amino-functionalized ddNTP analogue such as Pyrrolidine nucleoside triphosphates (prNTPs), and their polymerase activities with DNA polymerase by LC–MS and Gel-electrophoretic techniques. The Mass and PAGE analyses strongly support the incorporation of prNTPs into DNA oligonucleotide with Therminator DNA polymerase as like control substrate ddNTP. As resultant the DNA oligonucleotide are functionalized as amine group by prNTP incorporation with polymerase. Hence prNTPs provide opportunities to prepare demandable conjugated DNA with other biomolecules/dyes/fluorescence molecule without modifying nucleobase structure.

Amino acids bearing nucleobases for the synthesis of novel peptide nucleic acids

All of the four nucleobases found in DNA have been incorporated in their protected form into the 4-position of N-tert-butoxycarbonyl-L-proline methyl ester with cis-stereochemistry. An efficient route for the synthesis of N-tert-butoxycarbonyl-trans-4-hydroxy-D-proline methyl ester has been developed from which the enantiomers may be synthesized. In addition an efficient synthesis of N-tert-butoxycarbonyl-N-(2-hydroxyethyl)glycine methyl ester has been achieved and its hydroxy group replaced with protected nucleobases using the Mitsunobu reaction.