Abstract
The protected decapeptides pyroglutamyl-N im-benzylhistidyltryptophyl-O-benzylseryl-O-methyltyrosyl- glycylleucyl-NG-tosylarginylprolylglycine amide and pyroglutamylhistidyltryptophyl-O-benzylseryl-p nitrophenylalanylglycylleucyl-NG-tosylarginylprolylglycine amide were synthesized by solid-phase methods. They were converted to [5-(p-methoxyphenylalanine)]-LH-RH and [5-(p-nitrophenylalanine)]-LH-RH by reaction with sodium in liquid ammonia and anhydrous hydrogen fluoride, respectively Treatment of the p-nitrophenylalanine-protected peptide with sodium in liquid ammonia resulted in both the reduction of the nitro group to an amino group and the removal of the protecting groups to give [5-(p-aminophenylalanine)]-LH-RH in good yield. These analogs were assayed in vivo against pure natural LH-RH and found to possess the following LH-releasing activities: [5-(p-aminophenylalanine)]-LH-RH, 37%; [5-(p-methoxyphenylalanine)]-LH-RH, 24%; [5-(p-nitrophenylalanine)]-LH-RH, 5%.
| Original language | English |
|---|---|
| Pages (from-to) | 827-829 |
| Number of pages | 3 |
| Journal | Journal of Medicinal Chemistry |
| Volume | 16 |
| Issue number | 7 |
| State | Published - Dec 1 1973 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Analogs of luteinizing hormone-releasing hormone containing derivatives of phenylalanine in place of tyrosine. / Coy, David H.; Coy, Esther J.; Schally, Andrew V.
In: Journal of Medicinal Chemistry, Vol. 16, No. 7, 01.12.1973, p. 827-829.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Analogs of luteinizing hormone-releasing hormone containing derivatives of phenylalanine in place of tyrosine
AU - Coy, David H.
AU - Coy, Esther J.
AU - Schally, Andrew V
PY - 1973/12/1
Y1 - 1973/12/1
N2 - The protected decapeptides pyroglutamyl-N im-benzylhistidyltryptophyl-O-benzylseryl-O-methyltyrosyl- glycylleucyl-NG-tosylarginylprolylglycine amide and pyroglutamylhistidyltryptophyl-O-benzylseryl-p nitrophenylalanylglycylleucyl-NG-tosylarginylprolylglycine amide were synthesized by solid-phase methods. They were converted to [5-(p-methoxyphenylalanine)]-LH-RH and [5-(p-nitrophenylalanine)]-LH-RH by reaction with sodium in liquid ammonia and anhydrous hydrogen fluoride, respectively Treatment of the p-nitrophenylalanine-protected peptide with sodium in liquid ammonia resulted in both the reduction of the nitro group to an amino group and the removal of the protecting groups to give [5-(p-aminophenylalanine)]-LH-RH in good yield. These analogs were assayed in vivo against pure natural LH-RH and found to possess the following LH-releasing activities: [5-(p-aminophenylalanine)]-LH-RH, 37%; [5-(p-methoxyphenylalanine)]-LH-RH, 24%; [5-(p-nitrophenylalanine)]-LH-RH, 5%.
AB - The protected decapeptides pyroglutamyl-N im-benzylhistidyltryptophyl-O-benzylseryl-O-methyltyrosyl- glycylleucyl-NG-tosylarginylprolylglycine amide and pyroglutamylhistidyltryptophyl-O-benzylseryl-p nitrophenylalanylglycylleucyl-NG-tosylarginylprolylglycine amide were synthesized by solid-phase methods. They were converted to [5-(p-methoxyphenylalanine)]-LH-RH and [5-(p-nitrophenylalanine)]-LH-RH by reaction with sodium in liquid ammonia and anhydrous hydrogen fluoride, respectively Treatment of the p-nitrophenylalanine-protected peptide with sodium in liquid ammonia resulted in both the reduction of the nitro group to an amino group and the removal of the protecting groups to give [5-(p-aminophenylalanine)]-LH-RH in good yield. These analogs were assayed in vivo against pure natural LH-RH and found to possess the following LH-releasing activities: [5-(p-aminophenylalanine)]-LH-RH, 37%; [5-(p-methoxyphenylalanine)]-LH-RH, 24%; [5-(p-nitrophenylalanine)]-LH-RH, 5%.
UR - http://www.scopus.com/inward/record.url?scp=0015785858&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0015785858&partnerID=8YFLogxK
M3 - Article
C2 - 4579973
AN - SCOPUS:0015785858
VL - 16
SP - 827
EP - 829
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
SN - 0022-2623
IS - 7
ER -