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ACS Comb Sci DOI:10.1021/co200161z

Build/couple/pair strategy for the synthesis of stereochemically diverse macrolactams via head-to-tail cyclization.

Publication TypeJournal Article
Year of Publication2012
AuthorsFitzgerald, ME, Mulrooney, CA, Duvall, JR, Wei, J, Suh, B-C, Akella, LB, Vrcic, A, Marcaurelle, LA
JournalACS Comb Sci
Volume14
Issue2
Pages89-96
Date Published2012 Feb 13
ISSN2156-8944
KeywordsCyclization, Lactams, Macrocyclic, Solid-Phase Synthesis Techniques, Stereoisomerism
Abstract

A build/couple/pair (B/C/P) strategy was employed to generate a library of 7936 stereochemically diverse 12-membered macrolactams. All 8 stereoisomers of a common linear amine precursor were elaborated to form the corresponding 8 stereoisomers of two regioisomeric macrocyclic scaffolds via head-to-tail cyclization. Subsequently, these 16 scaffolds were further diversified via capping of two amine functionalities on SynPhase Lanterns. Reagents used for solid-phase diversification were selected using a sparse matrix design strategy with the aim of maximizing coverage of chemical space while adhering to a preset range of physicochemical properties.

DOI10.1021/co200161z
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/22252910?dopt=Abstract

Alternate JournalACS Comb Sci
PubMed ID22252910
PubMed Central IDPMC3289975
Grant ListUL1DE019585 / DE / NIDCR NIH HHS / United States
RL1HG004671 / HG / NHGRI NIH HHS / United States
RL1CA133834 / CA / NCI NIH HHS / United States
UL1 DE019585 / DE / NIDCR NIH HHS / United States
RL1GM084437 / GM / NIGMS NIH HHS / United States
P50 GM069721-11 / GM / NIGMS NIH HHS / United States
RL1 HG004671-05 / HG / NHGRI NIH HHS / United States
P50 GM069721 / GM / NIGMS NIH HHS / United States
RL1 GM084437 / GM / NIGMS NIH HHS / United States
RL1 HG004671 / HG / NHGRI NIH HHS / United States
RL1 CA133834 / CA / NCI NIH HHS / United States