N,O-isopropylidenated threonines as tools for peptide cyclization: Application to the synthesis of mahafacyclin B

Nima Sayyadi; Danielle Skropeta; Katrina A. Jolliffe

doi:10.1021/ol0522891

N,O-isopropylidenated threonines as tools for peptide cyclization: Application to the synthesis of mahafacyclin B

Nima Sayyadi, Danielle Skropeta, Katrina A. Jolliffe^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

(Chemical Equation Presented) The influence of a single N,O-isopropylidenated threonine turn-inducer on the cyclization of a linear heptapeptide precursor to mahafacyclin B has been investigated. Incorporation of an N,O-isopropylidenated threonine more than doubles the head-to-tail cyclization yield. The N,O-isopropylidene grouping is then readily disassembled to give the antimalarial cyclic peptide in high yield.

Original language	English
Pages (from-to)	5497-5499
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	24
DOIs	https://doi.org/10.1021/ol0522891
Publication status	Published - 24 Nov 2005
Externally published	Yes

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10.1021/ol0522891

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abstract = "(Chemical Equation Presented) The influence of a single N,O-isopropylidenated threonine turn-inducer on the cyclization of a linear heptapeptide precursor to mahafacyclin B has been investigated. Incorporation of an N,O-isopropylidenated threonine more than doubles the head-to-tail cyclization yield. The N,O-isopropylidene grouping is then readily disassembled to give the antimalarial cyclic peptide in high yield.",

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AU - Skropeta, Danielle

AU - Jolliffe, Katrina A.

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Y1 - 2005/11/24

N2 - (Chemical Equation Presented) The influence of a single N,O-isopropylidenated threonine turn-inducer on the cyclization of a linear heptapeptide precursor to mahafacyclin B has been investigated. Incorporation of an N,O-isopropylidenated threonine more than doubles the head-to-tail cyclization yield. The N,O-isopropylidene grouping is then readily disassembled to give the antimalarial cyclic peptide in high yield.

AB - (Chemical Equation Presented) The influence of a single N,O-isopropylidenated threonine turn-inducer on the cyclization of a linear heptapeptide precursor to mahafacyclin B has been investigated. Incorporation of an N,O-isopropylidenated threonine more than doubles the head-to-tail cyclization yield. The N,O-isopropylidene grouping is then readily disassembled to give the antimalarial cyclic peptide in high yield.

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N,O-isopropylidenated threonines as tools for peptide cyclization: Application to the synthesis of mahafacyclin B

Abstract

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