Literature DB >> 16354090

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

David C Cranfill1, Angel I Morales-Ramos, Mark A Lipton.   

Abstract

[structure: see text] The lipopeptide callipeltin D (1) was synthesized using an Fmoc-based solid-phase strategy in seven steps and 35% overall yield. The 1H NMR of synthetic 1 correlated closely with that of the natural product, confirming the configurational assignment of the novel amino acid constituent (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid.

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Year:  2005        PMID： 16354090      PMCID： PMC1635142          DOI： 10.1021/ol052438f

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


  6 in total

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

Authors:  Jason C Thoen; Angel I Morales-Ramos; Mark A Lipton
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

2.  Progress toward the total synthesis of callipeltin A (I): asymmetric synthesis of (3S,4R)-3,4-dimethylglutamine.

Authors:  B Liang; P J Carroll; M M Joullié
Journal:  Org Lett       Date:  2000-12-28       Impact factor: 6.005

3.  Synthesis of N-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine: An application of lanthanide-catalyzed transamidation.

Authors:  Selçuk Calimsiz; Mark A Lipton
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

4.  Asymmetric synthesis of four diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid: proof of configurational assignment.

Authors:  Jeffrey A Turk; Gonzalo S Visbal; Mark A Lipton
Journal:  J Org Chem       Date:  2003-10-03       Impact factor: 4.354

5.  2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage.

Authors:  K Barlos; O Chatzi; D Gatos; G Stavropoulos
Journal:  Int J Pept Protein Res       Date:  1991-06

6.  Application of 2-chlorotrityl resin in solid phase synthesis of (Leu15)-gastrin I and unsulfated cholecystokinin octapeptide. Selective O-deprotection of tyrosine.

Authors:  K Barlos; D Gatos; S Kapolos; C Poulos; W Schäfer; W Q Yao
Journal:  Int J Pept Protein Res       Date:  1991-12
  6 in total
  2 in total

1.  Solid-phase synthesis and configurational reassigment of callipeltin E. Implications for the structures of callipeltins A and B.

Authors:  Selçuk Calimsiz; Angel I Morales Ramos; Mark A Lipton
Journal:  J Org Chem       Date:  2006-08-18       Impact factor: 4.354

Review 2.  "Head-to-side-chain" cyclodepsipeptides of marine origin.

Authors:  Marta Pelay-Gimeno; Judit Tulla-Puche; Fernando Albericio
Journal:  Mar Drugs       Date:  2013-05-21       Impact factor: 5.118
  2 in total

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