Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Review | Special issue | Vol 77, No. 1, 2009, pp.67-83
Published online, 2nd June, 2008
DOI: 10.3987/REV-08-SR(F)1
Syntheses of Peptidyl Nucleoside Antibiotics

Hiroyuki Akita*

*Department of Pharmaceutical Sciences, Nihon Pharmaceutical University, , Japan


Polyoxins and nikkomycins are an important class of peptidyl nucleoside antibiotics isolated from the culture broths of Streptomyces cacaoi var. asoensis and Streptomyces tendae. For the syntheses of these antibiotics, efficient syntheses of 1-(5-amino-5-deoxy-β-D-allofurano-uronosyl)pyrimidines such as thymine polyoxin C, uracil polyoxin C and their congeners as a basic component corresponding to the right half were achieved based on the nucleophic 1,2-addition to methyl 2,3-O-isopropylidene-β-D-ribopentodialdo-1,4-furanoside. Then the syntheses of polyoxamic acid derivatives and their congeners corresponding to the left acid part were carried out based on 1,2-addition of carbon nucleophile to 4-O-protected-2,3-O-isopropylidene-L-threose. Coupling reaction of the activated ester derived from the left half acid part and amine part derived from the right half gave the N,O-protected peptidyl nucleoside congeners which were subjected to deprotection to afford polyoxins B, D, J, L, M, C and nikkomycin B.