TY - JOUR
T1 - On the Role of Tryptophan in Luteinizing‐Hormone‐Releasing Hormone (Luliberin)
AU - HAZUM, Eli
AU - FRIDKIN, Mati
AU - MEIDAN, Rina
AU - KOCH, Yitschak
PY - 1977/9
Y1 - 1977/9
N2 - The tryptophan residue of luteinizing‐hormone‐releasing hormone (luliberin) was chemically modified to produce the following analogs: [Trp(o)3]luliberin, Trp‐(2,4‐dinitrophenylsulfenyl)‐luliberin, Trp‐(2‐hydroxy‐5‐nitrobenzyl)luliberin, (Trp‐S‐luliberin)2, Trp‐CH3S‐luliberin and Trp‐formyl‐luliberin. The luteinizing‐hormone‐releasing activity of these analogs was determined by bioassay in vitro and found to be 0.2%, 0.2%, 0.6%, 1.5%, 1.7% and 7% of that of the natural hormone, respectively. These results demonstrate that alterations in the indole moiety of tryptophan‐3, which lead to a reduction in its electron density or sterically restrict its electron availability, are associated with a dramatic loss of biological activity.
AB - The tryptophan residue of luteinizing‐hormone‐releasing hormone (luliberin) was chemically modified to produce the following analogs: [Trp(o)3]luliberin, Trp‐(2,4‐dinitrophenylsulfenyl)‐luliberin, Trp‐(2‐hydroxy‐5‐nitrobenzyl)luliberin, (Trp‐S‐luliberin)2, Trp‐CH3S‐luliberin and Trp‐formyl‐luliberin. The luteinizing‐hormone‐releasing activity of these analogs was determined by bioassay in vitro and found to be 0.2%, 0.2%, 0.6%, 1.5%, 1.7% and 7% of that of the natural hormone, respectively. These results demonstrate that alterations in the indole moiety of tryptophan‐3, which lead to a reduction in its electron density or sterically restrict its electron availability, are associated with a dramatic loss of biological activity.
UR - http://www.scopus.com/inward/record.url?scp=0017655465&partnerID=8YFLogxK
U2 - 10.1111/j.1432-1033.1977.tb11806.x
DO - 10.1111/j.1432-1033.1977.tb11806.x
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C2 - 334545
AN - SCOPUS:0017655465
SN - 0014-2956
VL - 79
SP - 269
EP - 273
JO - European Journal of Biochemistry
JF - European Journal of Biochemistry
IS - 1
ER -