+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc alpha-amino acids

Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc alpha-amino acids

Organic Letters 6(15): 2627-2630

[reaction: see text] The solid-phase assembly of heterocyclic amino acids enabled the total synthesis of numerous diastereoisomers of tenuecyclamides A-D, establishing or correcting the stereochemistry of each natural product. This strategy provides a very efficient route to synthesize thiazole- and oxazole-containing macrolactams from heterocyclic amino acids that are readily prepared from Fmoc-alpha-amino acids. This methodology appears to be broadly applicable to the synthesis of natural product libraries incorporating unnatural heterocyclic amino acid residues for the purpose of drug discovery.

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 050335292

Download citation: RISBibTeXText

PMID: 15255707

DOI: 10.1021/ol049020m

Related references

Solid-phase synthesis of "mixed" peptidomimetics using Fmoc-protected aza-beta3-amino acids and alpha-amino acids. Journal of Organic Chemistry 70(26): 10701-8, 2005

Direct synthesis of glycosylated amino acids from carbohydrate peracetates and Fmoc amino acids: solid-phase synthesis of biomedicinally interesting glycopeptides. Methods in Enzymology 289: 221-245, 1997

Convenient and efficient synthesis of Boc-/Z-/Fmoc-beta-amino acids employing N-protected alpha-amino acid fluorides. Journal of Peptide Research 55(4): 289-294, 2000

Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-alpha-amino acids. Journal of Organic Chemistry 72(10): 3723-3728, 2007

Improved method for the synthesis of o glycosylated fmoc amino acids to be used in solid phase glycopeptide synthesis fmoc equals fluoren 9 ylmethoxycarbonyl. Journal of the Chemical Society Chemical Communications (14): 965-967, 1990

Synthesis of the glycosyl amino acids N alpha-Fmoc-Ser[Ac4-beta-D-Galp-(1-->3)-Ac2-alpha-D-GalN3p]-OPfp and N alpha-Fmoc-Thr[Ac4-beta-D-Galp-(1-->3)-Ac2-alpha-D-GalN3p]-OPfp and the application in the solid-phase peptide synthesis of multiply glycosylated mucin peptides with Tn and T antigenic structures. Carbohydrate Research 268(1): 17-34, 1995

Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with fmoc chemistry and aza-amino acids with heteroatomic side chains. Journal of Combinatorial Chemistry 7(6): 864-878, 2005

Metal chelating amino acids in the design of peptides and proteins Synthesis of N-alpha-Fmoc/Bu-t protected amino acids incorporating aminodiacetic acid moiety. Tetrahedron Letters 34(28): 4493-4496, 1993

An efficient conversion of the carboxylic group of N-Fmoc alpha-amino acids/peptide acids into N-formamides employing isocyanates as key intermediates. Journal of Organic Chemistry 72(25): 9804-9807, 2007

Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids. Organic Letters 3(8): 1201-1203, 2001

Solid phase peptide synthesis with fmoc amino acids an alternative protocol. Theodoropoulos, D (Ed ) Peptides, 1986; 19th European Symposium, Chalkidiki, Greece, August 31-September 5, 1986 Xix+684p Walter De Gruyter: Berlin, West Germany; New York, New York, Usa Illus 179-182, 1987

Solid-phase synthesis of bombesin by continuous flow procedure using Fmoc-amino acids. International Journal of Peptide and Protein Research 34(5): 423-429, 1989

Homologation of alpha-amino acids to beta-amino acids using Fmoc-amino acid pentafluorophenyl esters. Journal of Peptide Research 53(3): 308-313, 1999

Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis. Tetrahedron Letters 38(42): 7307-7310, 1997

Improved solid phase synthesis of bombesin by continuous flow procedure using fmoc amino acids. Regulatory Peptides 19(1-2): 137, 1987