Literature DB >> 11667621

The Kapakahines, Cyclic Peptides from the Marine Sponge Cribrochalina olemda.

Bryan K. S. Yeung1, Yoichi Nakao, Robin B. Kinnel, John R. Carney, Wesley Y. Yoshida, Paul J. Scheuer, Michelle Kelly-Borges.   

Abstract

Four cyclic peptides, kapakahines A-D, were isolated from the marine sponge Cribrochalina olemda. Their structures including complete stereochemistry were elucidated by spectral analysis and chemical degradation. The unique structural feature of these peptides is the lack of an amide linkage between two tryptophan residues. Instead the ring is closed by a bond from the indole nitrogen of Trp-1 to the beta-carbon of Trp-2.

Entities:  

Year:  1996        PMID: 11667621     DOI: 10.1021/jo960725e

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  18 in total

1.  Diversity of monomers in nonribosomal peptides: towards the prediction of origin and biological activity.

Authors:  Ségolène Caboche; Valérie Leclère; Maude Pupin; Gregory Kucherov; Philippe Jacques
Journal:  J Bacteriol       Date:  2010-08-06       Impact factor: 3.490

2.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

3.  Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines.

Authors:  Arijit A Adhikari; John D Chisholm
Journal:  Org Lett       Date:  2016-08-03       Impact factor: 6.005

Review 4.  Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.

Authors:  Vedanjali Gogineni; Mark T Hamann
Journal:  Biochim Biophys Acta Gen Subj       Date:  2017-08-24       Impact factor: 3.770

5.  Exploration of the interrupted Fischer indolization reaction.

Authors:  Alex W Schammel; Ben W Boal; Liansuo Zu; Tehetena Mesganaw; Neil K Garg
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

6.  Euryjanicin A: a new cycloheptapeptide from the Caribbean marine sponge Prosuberites laughlini.

Authors:  Jan Vicente; Brunilda Vera; Abimael D Rodríguez; Idaliz Rodríguez-Escudero; Raphael G Raptis
Journal:  Tetrahedron Lett       Date:  2009-08-12       Impact factor: 2.415

7.  Spiro fused diterpene-indole alkaloids from a creek-bottom-derived Aspergillus terreus.

Authors:  Shengxin Cai; Lin Du; Alexandra L Gerea; Jarrod B King; Jianlan You; Robert H Cichewicz
Journal:  Org Lett       Date:  2013-08-07       Impact factor: 6.005

8.  Direct, Enantioselective Synthesis of Pyrroloindolines and Indolines From Simple Indole Derivatives.

Authors:  Jane Ni; Haoxuan Wang; Sarah E Reisman
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

9.  Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores.

Authors:  N N Bhuvan Kumar; Olga A Mukhina; Andrei G Kutateladze
Journal:  J Am Chem Soc       Date:  2013-06-21       Impact factor: 15.419

10.  Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement.

Authors:  Xi-Shang Sun; Xing-Heng Wang; Hai-Yan Tao; Liang Wei; Chun-Jiang Wang
Journal:  Chem Sci       Date:  2020-09-17       Impact factor: 9.825

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