Literature DB >> 7503976

Novel microbial metabolites of the phoslactomycins family induce production of colony-stimulating factors by bone marrow stromal cells. II. Isolation, physico-chemical properties and structure determination.

T Kohama1, T Nakamura, T Kinoshita, I Kaneko, A Shiraishi.   

Abstract

Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of Streptomyces platensis SANK 60191 mainly by ethyl acetate extraction and preparative reverse-phase HPLC. The molecular weights and molecular formulae of LSNs A, B and C are 641: C32H52O10NP, 669: C34H56O10NP and 669: C34H56O10NP, respectively. The structure elucidation revealed that they belong to the phoslactomycin group antibiotics, and their structures contain an alpha,beta-unsaturated delta-lactone, an amino group, a phosphate ester and a cyclohexane ring moiety. The structures differ only at the substituent bound to the cyclohexane ring.

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Year:  1993        PMID： 7503976     DOI： 10.7164/antibiotics.46.1512

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


  15 in total

1.  Total synthesis and evaluation of cytostatin, its C10-C11 diastereomers, and additional key analogues: impact on PP2A inhibition.

Authors:  Brian G Lawhorn; Sobhana B Boga; Scott E Wolkenberg; David A Colby; Carla-Maria Gauss; Mark R Swingle; Lauren Amable; Richard E Honkanen; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

Review 2.  Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products.

Authors:  Barry M Trost; Joshua D Knopf; Cheyenne S Brindle
Journal:  Chem Rev       Date:  2016-12-08       Impact factor: 60.622

3.  Base-catalyzed direct aldolization of α-alkyl-α-hydroxy trialkyl phosphonoacetates.

Authors:  Michael T Corbett; Daisuke Uraguchi; Takashi Ooi; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

4.  Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence.

Authors:  Dong Gao; George A O'Doherty
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

5.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

6.  Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2010-11-18       Impact factor: 15.419

Review 7.  Genetic manipulation of the biosynthetic process leading to phoslactomycins, potent protein phosphatase 2A inhibitors.

Authors:  Mohini Ghatge; Nadaraj Palaniappan; Suparna Das Choudhuri; Kevin Reynolds
Journal:  J Ind Microbiol Biotechnol       Date:  2006-04-12       Impact factor: 3.346

8.  Polarity inversion of donor-acceptor cyclopropanes: disubstituted δ-lactones via enantioselective iridium catalysis.

Authors:  Joseph Moran; Austin G Smith; Ryan M Carris; Jeffrey S Johnson; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-10-31       Impact factor: 15.419

9.  Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  Org Lett       Date:  2011-05-17       Impact factor: 6.005

10.  Total synthesis, assignment of the relative and absolute stereochemistry, and structural reassignment of phostriecin (aka Sultriecin).

Authors:  Christopher P Burke; Nadia Haq; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-02-24       Impact factor: 15.419
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