Combinatorial modification of natural products: Preparation of unencoded and encoded libraries of Rauwolfia alkaloids

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 7, 1996, Pages 1097-1106

  Atuegbu, Andy ^a   Maclean, Derek ^a   Nguyen, Cindy ^a,b   Gordon, Eric M ^a,c   Jacobs, Jeffrey W ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

^b Argonaut Technologies   (United States)

^c Versicor Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CORYNANTHINE; NATURAL PRODUCT; RAUWOLFIA ALKALOID; RAUWOLSCINE; RESERPINE; YOHIMBINE;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; STEREOCHEMISTRY;

RAUVOLFIA;

EID: 0030182486     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00093-4     Document Type: Article

References (26)

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16. 10. Amino acids used in the preparation of libraries, followed in brackets by the binary code of secondary amines used in their encoding (encoding applicable to the acylated rauwolscinamide library only). The numerals one (1) and zero (0) represent the presence or absence, respectively, of a given diamine tag. The following secondary amines were used as molecular tags: N-methyl-N-heptylamine (MH), N-methyl-N-dodecylamine (MD), N-ethyl-N-butylamine (EB), N,N-dibutylamine (DB), N,N-dipentylamine (DP), and N,N-dihexylamine (DH). Tags are listed in the following order: MH, MD, EB, DB, DP, DH. Naturally occurring amino acids are designated by their conventional three-letter abbreviations. Side-chain protecting groups, if present, are indicated in parentheses. All of the amino acids were in their Fmoc-protected forms and L stereoconfigurations. Ala [000001], Asp(tBu) [000010], Gly [000011], Leu [000100], Lys-(Boc) [000101], norleucine [000110], Phe [000111], Trp(Boc) [001000], Thr(tBu) [001001], Tyr(tBu) [001010], Val [001011], His(Tos) [001100], Cys(Acm) [001101], γ-glutamic acid(tBu) [001110], His(Bzl) [010000], Arg(Tos) [010001], methionine sulfone [010010], dimethyl phosphotyrosine [010011], Ile [010100], Pro [010101], aminobutyric acid [010110], Glu(tBu) [011000], norvaline [011001], cyclohexylalanine [011010], p-benzoylphenylalanine [011100], citrulline [100000], 1-naphthylalanine [100100], methionine sulfoxide [100110], β-alanine [101000], p-aminophenylalanine(Boc) [101001], hydroxyproline(tBu) [101010], β-(2-thienyl)alanine [101100], 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid [110000], Ser(OAc) [110010], β-Asp(tBu) [110100], Scr(tBu) [111000].
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