Literature DB >> 8609083

FR901483, a novel immunosuppressant isolated from Cladobotryum sp. No. 11231. Taxonomy of the producing organism, fermentation, isolation, physico-chemical properties and biological activities.

K Sakamoto1, E Tsujii, F Abe, T Nakanishi, M Yamashita, N Shigematsu, S Izumi, M Okuhara.   

Abstract

FR901483, a novel immunosuppressant, has been isolated from the fermentation broth of Cladobotryum sp. No. 11231. The molecular formula of FR901483 has been determined as C20H31N2O6P. FR901483 exerts a potent immunosuppressive activity in vitro and significantly prolongs graft survival time in the rat skin allograft model. This compound has an intriguing tricyclic structure possessing a phosphate ester in its molecule. The ester residue may play an important role in exerting immunosuppressive activity because the desphosphoryl compound is devoid of activity. It is thought that the primary target of immunosuppression by this compound is inhibition of purine nucleotide biosynthesis.

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Year:  1996        PMID: 8609083     DOI: 10.7164/antibiotics.49.37

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  14 in total

1.  A Synthesis of the Tricyclic Core Structure of FR901483 Featuring an Ugi Four-Component Coupling and a Remarkably Selective Elimination Reaction.

Authors:  Hirofumi Seike; Erik J Sorensen
Journal:  Synlett       Date:  2008-03-18       Impact factor: 2.454

2.  Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon.

Authors:  Dimitar B Gotchev; Daniel L Comins
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

3.  Enantioselective Synthesis of the Tricyclic Core of FR901483 Featuring a Rh-Catalyzed [2+2+2] Cycloaddition.

Authors:  Stéphane Perreault; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2013       Impact factor: 3.157

Review 4.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

5.  Trianion synthon approach to spirocyclic heterocycles.

Authors:  Matthew A Perry; Richard R Hill; Scott D Rychnovsky
Journal:  Org Lett       Date:  2013-04-17       Impact factor: 6.005

6.  Studies on a total synthesis of the microbial immunosuppresive agent FR901483.

Authors:  Jeffrey E Kropf; Ivona C Meigh; Magnus W P Bebbington; Steven M Weinreb
Journal:  J Org Chem       Date:  2006-03-03       Impact factor: 4.354

7.  Toward the total synthesis of FR901483: concise synthesis of the azatricyclic skeleton.

Authors:  Suvi T M Simila; Stephen F Martin
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354

8.  Catalytic, asymmetric indolizidinone aza-quaternary stereocenter synthesis: expedient synthesis of the cylindricine alkaloid core.

Authors:  Derek M Dalton; Tomislav Rovis
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005

9.  Biosynthesis of the Immunosuppressant (-)-FR901483.

Authors:  Zhuan Zhang; Yui Tamura; Mancheng Tang; Tianzhang Qiao; Michio Sato; Yoshihiro Otsu; Satoshi Sasamura; Masatoshi Taniguchi; Kenji Watanabe; Yi Tang
Journal:  J Am Chem Soc       Date:  2020-12-29       Impact factor: 15.419

10.  Synthesis of crispine A analogues via an intramolecular Schmidt reaction.

Authors:  Ajoy Kapat; Ponminor Senthil Kumar; Sundarababu Baskaran
Journal:  Beilstein J Org Chem       Date:  2007-12-19       Impact factor: 2.883

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