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Synthesis and conformational studies of a Leu-enkephalin amide analogue containing a ferrocene substructure

Maricic, Suzana (author)
Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
Berg, Ulf (author)
Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
Frejd, Torbjörn (author)
Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
 (creator_code:org_t)
2002
2002
English.
In: Tetrahedron. - 0040-4020. ; 58:15, s. 3085-3093
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • Solution phase synthesis of a constrained Leu(5)-enkephalin amide analogue 10 is reported, in which the cyclic ferrocenyl containing subunit 7 was introduced as a mimetic of the tetrapeptide Tyr-Gly-Gly-Phe unit. Temperature dependence of the chemical shift of the amide protons of 10 indicated a hydrogen bond between the same amino acid residues as observed for the natural Leu-enkepalin in the single-bend conformation. The rotational barrier (DeltaG(c)(not equal)=16.8 kcal/mol) of the C-terminal amide group, which was determined by DNMR spectroscopy, and NOESY experiments indicated that the two termini were more distant as compared to the single-bend conformation of natural Leu-enkephalin amide. (C) 2002 Elsevier Science Ltd. All rights reserved.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Keyword

conformational analysis
ferrocene
cyclic peptide
beta-turn mimetic

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art (subject category)
ref (subject category)

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Maricic, Suzana
Berg, Ulf
Frejd, Torbjörn
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NATURAL SCIENCES
NATURAL SCIENCES
and Chemical Science ...
and Organic Chemistr ...
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Tetrahedron
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Lund University

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