Incorporation of the Unnatural Organometallic Amino Acid 1′‐Aminoferrocene‐1‐carboxylic Acid (Fca) into Oligopeptides by a Combination of Fmoc and Boc Solid‐Phase Synthetic Methods | Zendy

Barišić Lidija | Zendy; Rapić Vladimir | Zendy; MetzlerNolte Nils | Zendy

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Incorporation of the Unnatural Organometallic Amino Acid 1′‐Aminoferrocene‐1‐carboxylic Acid (Fca) into Oligopeptides by a Combination of Fmoc and Boc Solid‐Phase Synthetic Methods

Author(s) -

Barišić Lidija,

Rapić Vladimir,

MetzlerNolte Nils

Publication year - 2006

Publication title -

european journal of inorganic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 1434-1948

DOI - 10.1002/ejic.200600534

Subject(s) - chemistry , pentapeptide repeat , solid phase synthesis , amino acid , antiparallel (mathematics) , oligopeptide , stereochemistry , intramolecular force , carboxylic acid , peptide , hydrogen bond , peptide synthesis , group 2 organometallic chemistry , polymer chemistry , organic chemistry , molecule , biochemistry , physics , quantum mechanics , magnetic field

The organometallic amino acid 1′‐aminoferrocene‐1‐carboxylic acid (Fca) was incorporated internally into a peptide sequence by solid‐phase methods combining natural Fmoc‐protected amino acids and Boc‐Fca‐OH to give the pentapeptide Boc‐Fca‐Ala‐Gly‐Val‐Leu‐NH 2 ( 2 ) and the octapeptide Ac‐Val‐Gly‐Ala‐Fca‐Ala‐Gly‐Val‐Leu‐NH 2 ( 3 ). Compound 3 was found to have a helically ordered structure by NMR and CD spectroscopy, which is stabilized by intramolecular hydrogen bonding in an antiparallel β‐sheet‐like arrangement. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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