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Synthesis of a peptide nucleic acid with a novel 1-methyl-6-mercaptopurine base

✍ Scribed by Tarek Aboul-Fadl; Gopalan Rajeev; Arthur D. Broom

Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 596 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450223

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✦ Synopsis

Abstract

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A novel peptide nucleic acid (PNA) monomer 16 containing a novel 1‐methyl‐6‐mercaptopurine base was synthesized by coupling the in situ generated acid chloride of (1‐methyl‐6‐mercaptopurin‐9‐yl)acetic acid (6) into an L‐lysine backbone (13) using 10% CCl~4~ in pyridine and Ph~3~P. Compound 6 was synthesized from 6‐mercapto‐1‐methylpurine and ethylbromoacetate in the presence of NaH followed by alkaline hydrolysis and subsequent neutralization with a cation exchange resin. The L‐lysine backbone (13) was obtained by the reaction of Nϵ‐CBZ‐L‐lysine allyl ester with Boc‐aminoactaldehyde in the presence of NaBH~3~CN under reductive amination conditions. Oligomerization of the monomer 16 to PNA analogues was achieved using BOC‐BHA‐PEG‐PS resin as a solid support and the in situ generated acid chloride of 16 by 10% CCl~4~ in DCM in the presence of Ph~3~P.

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