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A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore.

ABSTRACT: Sulfonated molecules exhibit high water solubility, a property that is valuable for many biological applications but often complicates their synthesis and purification. Here we report a sulfonate protecting group that is resistant to nucleophilic attack but readily removed with trifluoroacetic acid (TFA). The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and the mild deprotection conditions allowed isolation of the product without requiring chromatography.

SUBMITTER: Pauff SM

PROVIDER: S-EPMC3627504 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore.

Pauff Steven M SM Miller Stephen C SC

The Journal of organic chemistry 20121213 2

Sulfonated molecules exhibit high water solubility, a property that is valuable for many biological applications but often complicates their synthesis and purification. Here we report a sulfonate protecting group that is resistant to nucleophilic attack but readily removed with trifluoroacetic acid (TFA). The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and the mild deprotection conditions allowed isolation of the product without requiring chromatograph ...[more]

PMID: 23167708

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