Site-specific N-alkylation of peptides on the solid phase

被引：89

作者：

Reichwein, JF ^{[1
]}

Liskamp, RMJ ^{[1
]}

机构：

[1] Univ Utrecht, Utrecht Inst Pharmaceut Sci, Dept Med Chem, NL-3508 TB Utrecht, Netherlands

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(97)10766-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient approach, featuring a Mitsunobu reaction, is described for the introduction of an alkyl group at a specific amide function of a peptide on the solid phase. This 'site-specific alkylation' procedure is illustrated with an N-ethyl scan of Leu-enkephalin. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1243 / 1246

页数：4

共 19 条

[11] Site-selective N-methylation of peptides on solid support [J].

Miller, SC ;

Scanlan, TS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2301-2302

[12] COMPARISON OF THE PROTEOLYTIC SUSCEPTIBILITIES OF HOMOLOGOUS L-AMINO-ACID, D-AMINO-ACID, AND N-SUBSTITUTED GLYCINE PEPTIDE AND PEPTOID OLIGOMERS [J].

MILLER, SM ;

SIMON, RJ ;

NG, S ;

ZUCKERMANN, RN ;

KERR, JM ;

MOOS, WH .

DRUG DEVELOPMENT RESEARCH, 1995, 35 (01) :20-32

[13] Solid phase synthesis of 1,3,4,7-tetrasubstituted perhydro-1,4-diazepine-2,5-diones [J].

Nefzi, A ;

Ostresh, JM ;

Houghten, RA .

TETRAHEDRON LETTERS, 1997, 38 (28) :4943-4946

[14]

PIETZONKA T, 1992, ANGEW CHEM INT EDIT, V31, P1481, DOI 10.1002/anie.199214811

[15] AN IMPROVED METHOD FOR ANCHORING OF 9-FLUORENYLMETHOXYCARBONYL-AMINO ACIDS TO 4-ALKOXYBENZYL ALCOHOL RESINS [J].

SIEBER, P .

TETRAHEDRON LETTERS, 1987, 28 (49) :6147-6150

[16] PEPTOIDS - A MODULAR APPROACH TO DRUG DISCOVERY [J].

SIMON, RJ ;

KANIA, RS ;

ZUCKERMANN, RN ;

HUEBNER, VD ;

JEWELL, DA ;

BANVILLE, S ;

NG, S ;

WANG, L ;

ROSENBERG, S ;

MARLOWE, CK ;

SPELLMEYER, DC ;

TAN, RY ;

FRANKEL, AD ;

SANTI, DV ;

COHEN, FE ;

BARTLETT, PA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (20) :9367-9371

[17] A reductive alkylation procedure applicable to both solution- and solid-phase syntheses of secondary amines [J].

Szardenings, AK ;

Burkoth, TS ;

Look, GC ;

Campbell, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6720-6722

[18] N,N,N',N'-TETRAMETHYLAZODICARBOXAMIDE (TMAD), A NEW VERSATILE REAGENT FOR MITSUNOBU REACTION - ITS APPLICATION TO SYNTHESIS OF SECONDARY-AMINES [J].

TSUNODA, T ;

OTSUKA, J ;

YAMAMIYA, Y ;

ITO, S .

CHEMISTRY LETTERS, 1994, (03) :539-542

[19] Pmc-protected amino acid esters as substrates in N-alkylamino acid synthesis. [J].

Wisniewski, K ;

Kolodziejczyk, AS .

TETRAHEDRON LETTERS, 1997, 38 (03) :483-486

← 1 2 →