Synthesis and biological properties of cholecystokinin heptapeptide analogues containing D- and L-forms of tert-leucine or neopentylglycine in position 5

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Title:Synthesis and biological properties of cholecystokinin heptapeptide analogues containing D- and L-forms of tert-leucine or neopentylglycine in position 5
Creators:
Hlaváček, Jan
Pírková, Jana
Pospíšek, Jan
Slaninová, Jiřina
Maletínská, Lenka
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 10, pp. 2209-2217

Abstract

Using solution or solid-phase synthesis we prepared the cholecystokinin fragment Boc-CCK-7 (Boc-Tyr-(SO<sub>3</sub><sup>-</sup>.Na<sup>+</sup>)-Met-Gly-Trp-Met-Asp-PheNH<sub>2</sub>) and its four analogues in which the methionine moiety (Met) in the carboxy-terminal part is replaced by tert-leucine (Tle) or neopentylglycine (Neo) residue or D-enantiomers of these non-coded amino acids. These structural modifications led to reduction of the studied biological activities (gall bladder contraction, anorectic activity, analgetic and sedation activity) of all prepared analogues except Boc[Neo<sup>5</sup>]-CCK-7 which, being less analgetically active, retains full gall bladder and sedation activity of CCK-8. Moreover, its anorectic activity is substantially higher (400%). This analogue is very interesting particularly for its selectively increased (4x) anorectic effect compared with that of CCK-8.

Title:Synthesis and biological properties of cholecystokinin heptapeptide analogues containing D- and L-forms of tert-leucine or neopentylglycine in position 5
Creators:
Hlaváček, Jan
Pírková, Jana
Pospíšek, Jan
Slaninová, Jiřina
Maletínská, Lenka
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:10
Page Range:pp. 2209-2217
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912209UNSPECIFIED
ID Code:5151
Item Type:Article
Deposited On:22 Feb 2010 11:31
Last Modified:22 Feb 2010 10:32

Citation

Hlaváček, Jan; Pírková, Jana; Pospíšek, Jan; Slaninová, Jiřina; Maletínská, Lenka (1991) Synthesis and biological properties of cholecystokinin heptapeptide analogues containing D- and L-forms of tert-leucine or neopentylglycine in position 5. Collection of Czechoslovak Chemical Communications, 56 (10). pp. 2209-2217. ISSN 0010-0765

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