A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes. Issue 25 (7th May 2019)

• Record Type: Journal Article
• Authors: Figliola, Carlotta; Marchal, Estelle; Groves, Brandon R.; Thompson, Alison
• Is Part Of: RSC advances. Volume 9:Issue 25(2019)
• Page Start: 14078
• Page End: 14092
• Publication Date: 2019-05-07
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9ra01435g
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. Abstract : Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the preparation of nine folate conjugates of the tripyrrolic prodigiosene skeleton. The strict requirement for step-wise construction of the folate core is demonstrated, so as to achieve conjugation at only the desired γ-carboxylic acid and thus maintain the α-carboxylic site for folate receptor (FRα) recognition. Linkages via ethylenediamine, polyethylene glycol and glutathione are demonstrated.