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Synthesis of Helicobacter pylori lipid A and its analogue using p-(trifluoromethyl)benzyl protecting group

✍ Scribed by Yasuhiro Sakai; Masato Oikawa; Hiroaki Yoshizaki; Tomohiko Ogawa; Yasuo Suda; Koichi Fukase; Shoichi Kusumoto *

Book ID
104210741
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
161 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

Synthesis of lipid A 1 isolated from Helicobacter pylori strain 206-1 has been achieved in 2.2% total yield through 14 steps from d-glucosamine by employing a p-(tri¯uoromethyl)benzyl group for protection of the hydroxy group on the 3-hydroxy fatty acid residue. The synthetic specimen was identical with the natural counterpart in chromatographic, spectroscopic, and biological aspects. A structural analogue 2 which lacks the ethanolamine residue of 1 was also synthesized, and 2 was found to exhibit less potent IL-1b-inducing activity than 1.

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✍ Peter Marbach; Josef Rudinger 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 877 KB

## Abstract [2‐__p__‐Fluorophenylalanine]oxytocin (**1a**), desamino‐[2‐__p__‐fluorophenylalanine]oxytocin (**1b**), and desamino‐oxytocin (**2**) have been synthesised __via__ intermediates containing S‐acetamidomethyl‐cysteine. The protected linear peptides were built up using both stepwise and f