Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and its enantiomer: a non-proteinogenic amino acid segment of the linear pentapeptide microginin

• Rajendra S. Rohokale and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2014, 10, 667–671, doi:10.3762/bjoc.10.59

• -amino acid fragment in AHDA 2a is also present in linear peptides such as bestatin and valinoctin [5][6][7][8], which are isolated from the same species. In addition, the chiral α-hydroxy-β-amino acid constituent is an important component of protein kinase inhibitor compounds like balanol and the

• -hydroxy-β-amino acid) in 2a is present in several biologically active compounds such as taxol, balanol and bestatin. Therefore, this methodology could be potentially exploited for the synthesis of the chiral segment of these compounds. Microginin (1) and (2S,3R)-AHDA (2a). Retrosynthetic analysis of AHDA

A unified approach to the important protein kinase inhibitor balanol and a proposed analogue

• Tapan Saha,
• Ratnava Maitra and
• Shital K. Chattopadhyay

Beilstein J. Org. Chem. 2013, 9, 2910–2915, doi:10.3762/bjoc.9.327

• Tapan Saha Ratnava Maitra Shital K. Chattopadhyay Department of Chemistry, University of Kalyani, Kalyani - 741235, West Bengal, India 10.3762/bjoc.9.327 Abstract A common approach to the important protein kinase inhibitor (−)-balanol and an azepine-ring-modified balanol derivative has been

• developed using an efficient fragment coupling protocol which proceeded in good overall yield. Keywords: azepane; balanol; Garner’s aldehyde; PKC inhibitor; ring-closing metathesis; Introduction Protein kinase C (PKC) is a family of phospholipid-dependent kinases that phosphorylate serine and threonine

• comprises of a number of isozymes and inappropriate activation of PKC has been linked to a variety of disorders [6][7]. The development of selective PKC inhibitors as novel therapeutics has therefore remained significant [8][9][10][11][12][13][14]. Balanol ((−)-1, Figure 1), a fungal metabolite [15] is