title: Novel sulfur-containing rapamycin analogs prepared by precursor-directed biosynthesis.
abstract: [reaction: see text] Two novel sulfur-containing analogs of the immunosuppressive natural product rapamycin (1) were obtained by feeding cultures of Streptomyces hygroscopicus with l-nipecotic acid (4) and either (S)-1,3-thiazane-4-carboxylic acid (5) or (S)-1,4-thiazane-3-carboxylic acid (6). The structures of the two new compounds, 20-thiarapamycin (2) and 15-deoxo-19-sulfoxylrapamycin (3), were determined by spectroscopic methods.
authors.affiliation: Department of Chemical & Screening Sciences, Wyeth Research, 401 North Middletown Road, Pearl River, New York 10965, USA. graziaei@wyeth.com
authors.forename: Edmund I
authors.initials: EI
authors.lastname: Graziani
authors.forename: Frank V
authors.initials: FV
authors.lastname: Ritacco
authors.forename: Mia Y
authors.initials: MY
authors.lastname: Summers
authors.forename: T Mark
authors.initials: TM
authors.lastname: Zabriskie
authors.forename: Ker
authors.initials: K
authors.lastname: Yu
authors.forename: Valerie S
authors.initials: VS
authors.lastname: Bernan
authors.forename: Michael
authors.initials: M
authors.lastname: Greenstein
authors.forename: Guy T
authors.initials: GT
authors.lastname: Carter
mesh_terms: D007166:Immunosuppressive Agents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D020123:Sirolimus / Q000031:analogs & derivatives* / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*
chemical_list: D007166:Immunosuppressive Agents; D013455:Sulfur; D020123:Sirolimus