Synthesis of chromogenic arginine derivatives as substrates for trypsin

Robert E. Plapinger, Marvin M. Nachlas, Myron L. Seligman, Arnold M. Seligman

Research output: Contribution to journalArticle

Abstract

The synthesis of 15 chromogenic substrates which are split rapidly by trypsin is described. All are derivatives of arginine and were prepared by the mixed anhydride method utilizing the protonation blocking procedure for masking the guanidine group. The three substrates most rapidly hydrolyzed are Nα-carbobenzoxyglycylglycyl-L-arginine-2-naphthylamide hydrochloride, β-carboxyproprionyl-L-arginyl-L-arginine-2-naphthylamide dihydrochloride, and Nα-carbobenzoxy-L-arginyl-L-arginyl-L-arginine-2-naphthylamide trihydrochloride.

Original languageEnglish (US)
Pages (from-to)1781-1785
Number of pages5
JournalJournal of Organic Chemistry
Volume30
Issue number6
StatePublished - 1965

Fingerprint

Chromogenics
arginylarginine
Trypsin
Arginine
Derivatives
Substrates
Chromogenic Compounds
Anhydrides
Protonation
Guanidine
2-naphthylamide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Plapinger, R. E., Nachlas, M. M., Seligman, M. L., & Seligman, A. M. (1965). Synthesis of chromogenic arginine derivatives as substrates for trypsin. Journal of Organic Chemistry, 30(6), 1781-1785.

Synthesis of chromogenic arginine derivatives as substrates for trypsin. / Plapinger, Robert E.; Nachlas, Marvin M.; Seligman, Myron L.; Seligman, Arnold M.

In: Journal of Organic Chemistry, Vol. 30, No. 6, 1965, p. 1781-1785.

Research output: Contribution to journalArticle

Plapinger, RE, Nachlas, MM, Seligman, ML & Seligman, AM 1965, 'Synthesis of chromogenic arginine derivatives as substrates for trypsin', Journal of Organic Chemistry, vol. 30, no. 6, pp. 1781-1785.
Plapinger RE, Nachlas MM, Seligman ML, Seligman AM. Synthesis of chromogenic arginine derivatives as substrates for trypsin. Journal of Organic Chemistry. 1965;30(6):1781-1785.
Plapinger, Robert E. ; Nachlas, Marvin M. ; Seligman, Myron L. ; Seligman, Arnold M. / Synthesis of chromogenic arginine derivatives as substrates for trypsin. In: Journal of Organic Chemistry. 1965 ; Vol. 30, No. 6. pp. 1781-1785.
@article{94fea57e9ea849c199e4badeb80da6ec,
title = "Synthesis of chromogenic arginine derivatives as substrates for trypsin",
abstract = "The synthesis of 15 chromogenic substrates which are split rapidly by trypsin is described. All are derivatives of arginine and were prepared by the mixed anhydride method utilizing the protonation blocking procedure for masking the guanidine group. The three substrates most rapidly hydrolyzed are Nα-carbobenzoxyglycylglycyl-L-arginine-2-naphthylamide hydrochloride, β-carboxyproprionyl-L-arginyl-L-arginine-2-naphthylamide dihydrochloride, and Nα-carbobenzoxy-L-arginyl-L-arginyl-L-arginine-2-naphthylamide trihydrochloride.",
author = "Plapinger, {Robert E.} and Nachlas, {Marvin M.} and Seligman, {Myron L.} and Seligman, {Arnold M.}",
year = "1965",
language = "English (US)",
volume = "30",
pages = "1781--1785",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "6",

}

TY - JOUR

T1 - Synthesis of chromogenic arginine derivatives as substrates for trypsin

AU - Plapinger, Robert E.

AU - Nachlas, Marvin M.

AU - Seligman, Myron L.

AU - Seligman, Arnold M.

PY - 1965

Y1 - 1965

N2 - The synthesis of 15 chromogenic substrates which are split rapidly by trypsin is described. All are derivatives of arginine and were prepared by the mixed anhydride method utilizing the protonation blocking procedure for masking the guanidine group. The three substrates most rapidly hydrolyzed are Nα-carbobenzoxyglycylglycyl-L-arginine-2-naphthylamide hydrochloride, β-carboxyproprionyl-L-arginyl-L-arginine-2-naphthylamide dihydrochloride, and Nα-carbobenzoxy-L-arginyl-L-arginyl-L-arginine-2-naphthylamide trihydrochloride.

AB - The synthesis of 15 chromogenic substrates which are split rapidly by trypsin is described. All are derivatives of arginine and were prepared by the mixed anhydride method utilizing the protonation blocking procedure for masking the guanidine group. The three substrates most rapidly hydrolyzed are Nα-carbobenzoxyglycylglycyl-L-arginine-2-naphthylamide hydrochloride, β-carboxyproprionyl-L-arginyl-L-arginine-2-naphthylamide dihydrochloride, and Nα-carbobenzoxy-L-arginyl-L-arginyl-L-arginine-2-naphthylamide trihydrochloride.

UR - http://www.scopus.com/inward/record.url?scp=0041771538&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0041771538&partnerID=8YFLogxK

M3 - Article

C2 - 14325493

AN - SCOPUS:0041771538

VL - 30

SP - 1781

EP - 1785

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 6

ER -