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Literature DB >> 23136451

Biomimetic Synthesis of Cbz-(S)-Dolaphenine.

Pablo García-Reynaga¹, Michael S Vannieuwenhze.

Abstract

A new route to Cbz-(S)-dolaphenine, a recurring element in bioactive peptidic natural products, has been implemented, which closely parallels the biogenetic pathway. Cyclodehydration of 11 to yield thiazoline 2 allows for a Ni(0)-promoted decarbonylative aromatization to provide the thiazole framework with retention of stereochemistry.

Entities: CellLine Chemical Disease Gene Species

Year: 2012 PMID： 23136451 PMCID： PMC3488445 DOI： 10.1016/j.tetlet.2012.07.027

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

17 in total

Review 1. Thiazole and oxazole peptides: biosynthesis and molecular machinery.

Authors: R S Roy; A M Gehring; J C Milne; P J Belshaw; C T Walsh
Journal: Nat Prod Rep Date: 1999-04 Impact factor: 13.423

2. Thermophilic, reversible gamma-resorcylate decarboxylase from Rhizobium sp. strain MTP-10005: purification, molecular characterization, and expression.

Authors: Masahiro Yoshida; Nobuhiro Fukuhara; Tadao Oikawa
Journal: J Bacteriol Date: 2004-10 Impact factor: 3.490

Review 3. Marine natural products as anticancer drugs.

Authors: T Luke Simmons; Eric Andrianasolo; Kerry McPhail; Patricia Flatt; William H Gerwick
Journal: Mol Cancer Ther Date: 2005-02 Impact factor: 6.261

4. Phase II study of dolastatin-10 in patients with hormone-refractory metastatic prostate adenocarcinoma.

Authors: U Vaishampayan; M Glode; W Du; A Kraft; G Hudes; J Wright; M Hussain
Journal: Clin Cancer Res Date: 2000-11 Impact factor: 12.531

Review 5. Biosynthesis of aminovinyl-cysteine-containing peptides and its application in the production of potential drug candidates.

Authors: Clarissa S Sit; Sabesan Yoganathan; John C Vederas
Journal: Acc Chem Res Date: 2011-03-02 Impact factor: 22.384

6. Decarbonylative approach to the synthesis of enamides from amino acids: stereoselective synthesis of the (Z)-aminovinyl-D-cysteine unit of mersacidin.

Authors: Pablo García-Reynaga; Angela K Carrillo; Michael S VanNieuwenhze
Journal: Org Lett Date: 2012-02-01 Impact factor: 6.005

7. Dolastatin 10, a powerful cytostatic peptide derived from a marine animal. Inhibition of tubulin polymerization mediated through the vinca alkaloid binding domain.

Authors: R Bai; G R Pettit; E Hamel
Journal: Biochem Pharmacol Date: 1990-06-15 Impact factor: 5.858

8. Characterization of a novel type of oxidative decarboxylase involved in the biosynthesis of the styryl moiety of chondrochloren from an acylated tyrosine.

Authors: Shwan Rachid; Ole Revermann; Christina Dauth; Uli Kazmaier; Rolf Müller
Journal: J Biol Chem Date: 2010-01-15 Impact factor: 5.157