Literature DB >> 12465911

Synthesis of the unnatural amino acid AGDHE, a constituent of the cyclic depsipeptides callipeltins A and D.

Jason C Thoen1, Angel I Morales-Ramos, Mark A Lipton.   

Abstract

[reaction: see text] The novel amino acid residue (2R,3R,4S)-4-amido-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE, 3), a constituent of the cyclic depsipeptides callipeltins A and D, and its (2S,3S,4S) diastereomer were synthesized from a protected L-ornithine derivative in 13 steps (15% overall yield), and its configurational assignment was reexamined by (1)H NMR.

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Year:  2002        PMID： 12465911      PMCID： PMC1905820          DOI： 10.1021/ol0269852

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Callipeltin A, a cyclic depsipeptide inhibitor of the cardiac sodium-calcium exchanger and positive inotropic agent.

Authors:  L Trevisi; S Bova; G Cargnelli; D Danieli-Betto; M Floreani; E Germinario; M V D'Auria; S Luciani
Journal:  Biochem Biophys Res Commun       Date:  2000-12-09       Impact factor: 3.575

2.  Synthesis of the C(26)-C(32) Oxazole Fragment of Calyculin C: A Test Case for Oxazole Syntheses.

Authors:  Petri M. Pihko; Ari M. P. Koskinen
Journal:  J Org Chem       Date:  1998-01-09       Impact factor: 4.354

3.  Inhibition of aspartic proteinases by peptides containing lysine and ornithine side-chain analogues of statine.

Authors:  F G Salituro; N Agarwal; T Hofmann; D H Rich
Journal:  J Med Chem       Date:  1987-02       Impact factor: 7.446
  3 in total
  5 in total

1.  Solid-phase synthesis of callipeltin D. Stereochemical confirmation of the unnatural amino acid AGDHE.

Authors:  David C Cranfill; Angel I Morales-Ramos; Mark A Lipton
Journal:  Org Lett       Date:  2005-12-22       Impact factor: 6.005

2.  Complete stereochemistry of neamphamide A and absolute configuration of the beta-methoxytyrosine residue in papuamide B.

Authors:  Naoya Oku; Ravi Krishnamoorthy; Alan G Benson; Robert L Ferguson; Mark A Lipton; Lawrence R Phillips; Kirk R Gustafson; James B McMahon
Journal:  J Org Chem       Date:  2005-08-19       Impact factor: 4.354

3.  Theopapuamide, a cyclic depsipeptide from a Papua New Guinea lithistid sponge Theonella swinhoei.

Authors:  Anokha S Ratnayake; Tim S Bugni; Xidong Feng; Mary Kay Harper; Jack J Skalicky; Kaleem A Mohammed; Cynthia D Andjelic; Louis R Barrows; Chris M Ireland
Journal:  J Nat Prod       Date:  2006-11       Impact factor: 4.050

4.  Cyclodepsipeptides from marine sponges: natural agents for drug research.

Authors:  Gowri Shankar Bagavananthem Andavan; Rosa Lemmens-Gruber
Journal:  Mar Drugs       Date:  2010-03-22       Impact factor: 5.118

5.  Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography-electrospray ionization mass spectrometry.

Authors:  Sonja Hess; Kirk R Gustafson; Dennis J Milanowski; Edgardo Alvira; Mark A Lipton; Lewis K Pannell
Journal:  J Chromatogr A       Date:  2004-05-07       Impact factor: 4.759
  5 in total

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