Solid-phase SN2 macrocyclization reactions to form beta-turn mimics. Academic Article

abstract

• [formula: see text] Efficient solid-phase SN2 macrocyclization reactions were sought to facilitate preparations of focused libraries of beta-turn mimetics. A very efficient, but undesired, cyclization reaction to give five-membered ring lactams 4 was identified in attempts to use O-nucleophiles. Subsequent studies focused exclusively on S-nucleophiles. These reactions gave the desired macrocyclization products 1 in high purities and good overall yields. Conformational analyses of illustrative macrocyclization products 1 via NMR, CD, and molecular simulations showed that they seem to sample both type I and type II beta-turn conformations in solution. CD studies indicate a curious relationship between the preferred conformation and the amino acids encapsulated in the macrocycles.

authors

• Burgess, Kevin

published proceedings

• Org Lett

altmetric score

• 9

author list (cited authors)

• Feng, Y., Pattarawarapan, M., Wang, Z., & Burgess, K.

citation count

• 49

complete list of authors

• Feng, Y||Pattarawarapan, M||Wang, Z||Burgess, K

publication date

• July 1999

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Beta-lactams
• Chromatography, High Pressure Liquid
• Circular Dichroism
• Cyclization
• Molecular Mimicry
• Peptides
• Protein Conformation
• Proteins
• Serine
• Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

PubMed Central ID

• 10822547

Digital Object Identifier (DOI)

• 10.1021/ol990597r

start page

• 121

end page

• 124

volume

• 1

issue

• 1

URL

• http://dx.doi.org/10.1021/ol990597r