Homotyrosine

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Structural formula
Structural formula of homotyrosine
Structural formula of homotyrosine without specifying the stereochemistry
General
Surname Homotyrosine
other names
  • α-homotyrosine
  • α-amino-4- (4-hydroxyphenyl) butyric acid
  • Hty
  • hTyr
Molecular formula C 10 H 13 NO 3
External identifiers / databases
CAS number
  • 185062-84-4 (unspec.)
  • 221243-01-2 [( S ) -enantiomer]
  • 749828-81-7 [( R ) -enantiomer]
PubChem 4153395
ChemSpider 3365526
Wikidata Q27287572
properties
Molar mass 195.21 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Homotyrosine is a non-proteinogenic amino acid and an analogue of the proteinogenic amino acid tyrosine .

Isomers

Homotyrosine has a stereocenter , so there are two enantiomers . When homotyrosine is mentioned in the scientific literature without a prefix, it is usually L- homotyrosine that is meant. Its enantiomer - i.e. D -homotyrosine - is of only marginal importance.

Isomers of homotyrosine
Surname L -homotyrosine D -homotyrosine
other names (+) - homotyrosine
( S ) -homotyrosine		 (-) - Homotyrosine
( R ) -homotyrosine
Structural formula L-Homotyrosine.svg D-Homotyrosine.svg
CAS number 221243-01-2 749828-81-7
185062-84-4 (unspec.)
PubChem 15160483 40429052
4153395 (unspec.)
Wikidata Q27155634 Q27259811
Q27287572 (unspec.)

properties

L- homotyrosine is formed by the blue-green alga Planktothrix rubescens and incorporated into two microcystins ( MC-Hty Y and MC-HtyHty ) by non-ribosomal peptide synthetases . It is also used by Anabaena sp. 66 formed and incorporated into microcystins ([Dha7] -microcystin-HtyR, [D-Asp3, Dha7] -microcystin-HtyR and [L-Ser7] microcystin-HtyR). It also occurs in the fungicidal substances Echinocandin B and Pneumocandin B 0 .

L- homotyrosine is used as an analogue of tyrosine in peptide synthesis .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ HS Okumura, B. Philmus, C. Portmann, TK Hemscheidt: Homotyrosine-containing cyanopeptolins 880 and 960 and anabaenopeptins 908 and 915 from Planktothrix agardhii CYA 126/8. In: Journal of Natural Products . Volume 72, number 1, January 2009, pp. 172-176, doi : 10.1021 / np800557m , PMID 19115837 , PMC 2673918 (free full text).
  3. ↑ G. Christiansen, WY Yoshida, JF Blom, C. Portmann, K. Gademann, T. Hemscheidt, R. Kurmayer: Isolation and structure determination of two microcystins and sequence comparison of the McyABC adenylation domains in Planktothrix species. In: Journal of Natural Products . Volume 71, number 11, November 2008, pp. 1881-1886, doi : 10.1021 / np800397u , PMID 18939865 , PMC 3080429 (free full text).
  4. ↑ M. Namikoshi, K. Sivonen, WR Evans, WW Carmichael, L. Rouhiainen, R. Luukkainen, KL Rinehart: Structures of three new homotyrosine-containing microcystins and a new homophenylalanine variant from Anabaena sp. strain 66. In: Chemical Research in Toxicology . Volume 5, Number 5, 1992 Sep-Oct, pp. 661-666, PMID 1446006 .
  5. ↑ Current Medicinal Chemistry . (1999), Volume 6, Issue 12, p. 1179 ( limited preview in the Google book search).
  6. ^ Current Pharmaceutical Design . (1999), Volume 5, Issue 2, p. 68 ( limited preview in the Google book search).