RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2006(16): 2789-2793
DOI: 10.1055/s-2006-942485
DOI: 10.1055/s-2006-942485
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 4-(Fmoc-aminoacyloxymethyl)phenoxyacetic Acids for Use in Solid-Phase Peptide Synthesis
Weitere Informationen
Received
7 April 2006
Publikationsdatum:
12. Juli 2006 (online)
Publikationsverlauf
Publikationsdatum:
12. Juli 2006 (online)

Abstract
The synthesis of 4-(Fmoc-aminoacyloxymethyl)phenoxyacetic acids was achieved in high yield by the reaction of Fmoc-amino acids with (4-iodomethylphenoxy)acetic acid 2-oxo-2-phenylethyl ester. The removal of the temporary protecting group, phenacyl ester, was effectively achieved by reductive cleavage with magnesium turnings.
Key words
solid-phase synthesis - magnesium - peptides
- 1
Merrifield RB. J. Am. Chem. Soc. 1963, 85: 2145 -
2a
Chan WC.White PD. Fmoc Solid Phase Peptide Synthesis OUP; Oxford: 2000. -
2b
Fields GB. Methods in Enzymology Vol. 289: Academic Press; New York: 1997. - 3
Wang S.-S. J. Am. Chem. Soc. 1973, 95: 1328 - 4
Wang S.-S.Tam JP.Wang BSH.Merrifield RB. Int. J. Pept. Protein Res. 1981, 18: 459 - 5
Atherton E.Logan CJ.Shepard RC. J. Chem. Soc., Perkin Trans. 1 1981, 538 - 6
Shepard RC.Williams BJ. Int. J. Pept. Protein Res. 1982, 20: 451 - 7
Atherton E.Benoiton NL.Brown E.Sheppard RC.Williams BJ. J. Chem. Soc., Chem. Commun. 1981, 336 - 8
Atherton E.Logan CJ.Sheppard RC. J. Chem. Soc., Perkin Trans. 1 1981, 538 - 9
Bernatowicz MS.Kearney T.Neves RS.Köster H. Tetrahedron Lett. 1989, 30: 4341 - 10
Mitchell AR.Kent SBH.Engelhard M.Merrifield RB. J. Org. Chem. 1978, 43: 2845 -
11a
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: J. Wiley & Sons; New York: 1999. p.393-394 -
11b
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: J. Wiley & Sons; New York: 1999. p.728 - 12
Kokinaki S.Leondiadis L.Ferderigos N. Org. Lett. 2005, 7: 1723 - 13
Stelakatos GC.Zervas L. J. Chem. Soc. C 1966, 1191 - 14
Olah GA.Narang SC.Balaram Gupta BG.Malhotra R. J. Org. Chem. 1979, 44: 1247 - 15
Tam JP.Kent SBH.Wong TW.Merrifield RB. Synthesis 1980, 955 - 16
Clark JH.Miller M. Tetrahedron Lett. 1977, 599 - 17
Wang S.-S.Gisin BF.Winter DP.Makofske R.Kulesha ID.Tzougraki C.Meienhofer J. J. Org. Chem. 1977, 42: 1286 - 18
Hendrickson JB.Kandall C. Tetrahedron Lett. 1970, 343 - 19
Zikos CC.Ferderigos N. Tetrahedron Lett. 1995, 36: 3741 - 21
Chang CD.Waki M.Ahmad M.Meienhofer J.Lundell EO.Haug JD. Int. J. Pept. Protein Res. 1980, 15: 59
References
Benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate.