Cyclic Melanotropins, Part Vi*. Reverse Phase Hplc Studies

M. Lebl, W. L. Cody, Victor J Hruby

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The chromatographic behavior of 17 cyclic [Cys, Cys]-a-melanocyte stimulating hormone (a-MSH, a-melanotropin) analogs were studied on two reversed phase columns (Altech and Vydac) using several mobile phases. It was observed that analogs which contain a D-amino acid were always eluted earlier than the corresponding L-amino acid-containing analogues. Substitution of penicillamine for cysteine in the 4 position led to a more lipophilic compound as expected, but when penicillamine was substituted in the 10 position, apparently a less lipophilic compound resulted. These observations can be interpreted as a result of a conformational change in the molecule caused by the particular substitution. Furthermore, decreasing the size of the intramolecular disulfide ring led to a decrease in lipophilicity (i.e. retention time). The carba modification of the disulfide bridge had a similar effect as previously seen in oxytocin and vasopressin, that is, a decrease in retention time.

Original languageEnglish (US)
Pages (from-to)1195-1210
Number of pages16
JournalJournal of Liquid Chromatography
Volume7
Issue number6
DOIs
StatePublished - May 1 1984

Fingerprint

Melanocyte-Stimulating Hormones
Disulfides
Substitution reactions
Amino Acids
Penicillamine
Oxytocin
Vasopressins
Molecules

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Cyclic Melanotropins, Part Vi*. Reverse Phase Hplc Studies. / Lebl, M.; Cody, W. L.; Hruby, Victor J.

In: Journal of Liquid Chromatography, Vol. 7, No. 6, 01.05.1984, p. 1195-1210.

Research output: Contribution to journalArticle

@article{6bb2b94936254990834588034685e374,
title = "Cyclic Melanotropins, Part Vi*. Reverse Phase Hplc Studies",
abstract = "The chromatographic behavior of 17 cyclic [Cys, Cys]-a-melanocyte stimulating hormone (a-MSH, a-melanotropin) analogs were studied on two reversed phase columns (Altech and Vydac) using several mobile phases. It was observed that analogs which contain a D-amino acid were always eluted earlier than the corresponding L-amino acid-containing analogues. Substitution of penicillamine for cysteine in the 4 position led to a more lipophilic compound as expected, but when penicillamine was substituted in the 10 position, apparently a less lipophilic compound resulted. These observations can be interpreted as a result of a conformational change in the molecule caused by the particular substitution. Furthermore, decreasing the size of the intramolecular disulfide ring led to a decrease in lipophilicity (i.e. retention time). The carba modification of the disulfide bridge had a similar effect as previously seen in oxytocin and vasopressin, that is, a decrease in retention time.",
author = "M. Lebl and Cody, {W. L.} and Hruby, {Victor J}",
year = "1984",
month = "5",
day = "1",
doi = "10.1080/01483918408074037",
language = "English (US)",
volume = "7",
pages = "1195--1210",
journal = "Journal of Liquid Chromatography and Related Technologies",
issn = "1082-6076",
publisher = "Taylor and Francis Ltd.",
number = "6",

}

TY - JOUR

T1 - Cyclic Melanotropins, Part Vi*. Reverse Phase Hplc Studies

AU - Lebl, M.

AU - Cody, W. L.

AU - Hruby, Victor J

PY - 1984/5/1

Y1 - 1984/5/1

N2 - The chromatographic behavior of 17 cyclic [Cys, Cys]-a-melanocyte stimulating hormone (a-MSH, a-melanotropin) analogs were studied on two reversed phase columns (Altech and Vydac) using several mobile phases. It was observed that analogs which contain a D-amino acid were always eluted earlier than the corresponding L-amino acid-containing analogues. Substitution of penicillamine for cysteine in the 4 position led to a more lipophilic compound as expected, but when penicillamine was substituted in the 10 position, apparently a less lipophilic compound resulted. These observations can be interpreted as a result of a conformational change in the molecule caused by the particular substitution. Furthermore, decreasing the size of the intramolecular disulfide ring led to a decrease in lipophilicity (i.e. retention time). The carba modification of the disulfide bridge had a similar effect as previously seen in oxytocin and vasopressin, that is, a decrease in retention time.

AB - The chromatographic behavior of 17 cyclic [Cys, Cys]-a-melanocyte stimulating hormone (a-MSH, a-melanotropin) analogs were studied on two reversed phase columns (Altech and Vydac) using several mobile phases. It was observed that analogs which contain a D-amino acid were always eluted earlier than the corresponding L-amino acid-containing analogues. Substitution of penicillamine for cysteine in the 4 position led to a more lipophilic compound as expected, but when penicillamine was substituted in the 10 position, apparently a less lipophilic compound resulted. These observations can be interpreted as a result of a conformational change in the molecule caused by the particular substitution. Furthermore, decreasing the size of the intramolecular disulfide ring led to a decrease in lipophilicity (i.e. retention time). The carba modification of the disulfide bridge had a similar effect as previously seen in oxytocin and vasopressin, that is, a decrease in retention time.

UR - http://www.scopus.com/inward/record.url?scp=84916094060&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84916094060&partnerID=8YFLogxK

U2 - 10.1080/01483918408074037

DO - 10.1080/01483918408074037

M3 - Article

VL - 7

SP - 1195

EP - 1210

JO - Journal of Liquid Chromatography and Related Technologies

JF - Journal of Liquid Chromatography and Related Technologies

SN - 1082-6076

IS - 6

ER -