Synthesis of 3-Guaninyl-and 3-Adeninyl-5-hydroxymethyl-2-pyrrolidinone Nucleosides

…, JG D'Angelo, MD Morton, J Quinn…

Index: Saleh, Abdullah; D'Angelo, John G.; Morton, Martha D.; Quinn, Jesse; Redden, Kendra; Mielguz, Rafal W.; Pavlik, Christopher; Smith, Michael B. Journal of Organic Chemistry, 2011 , vol. 76, # 14 p. 5574 - 5583

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Citation Number: 7

Abstract

l-And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5- hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

Efficient total synthesis of AI-77-B, a gastroprotective substance from Bacillus pumilus AI-77

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Structural Prerequisites for Receptor Binding of Helicokinin I, a Diuretic Insect Neuropeptide from Helicoverpa zea

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