Side reaction with N-carboxymethyl amino acids in the synthesis of backbone cyclized peptides

被引：3

作者：

Besser, D ^{[1
]}

Greiner, G ^{[1
]}

Reissmann, S ^{[1
]}

机构：

[1] Univ Jena, Inst Biochem & Biophys, D-07743 Jena, Germany

来源：

LETTERS IN PEPTIDE SCIENCE | 1998年 / 5卷 / 04期

关键词：

backbone cyclization; bradykinin; branched building units; diketopiperazine formation;

D O I：

10.1007/BF02443547

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The use of N-carboxymethyl amino acids in the assembly of peptides with backbone cyclization can lead to diketopiperazine formation by intramolecular aminolysis which occurs despite the tert-butyl protection of the carboxy group. This undesired side reaction can be prevented by a very short deprotection time for the Fmoc group, by elongation of the N-carboxyalkyl chain or by forming the backbone (lactam) bridge before Fmoc removal, but not by the use of DBU or additives.

引用

页码：299 / 303

页数：5

共 50 条

[21] STUDIES OF UNUSUAL AMINO-ACIDS AND THEIR PEPTIDES .12. THE CHEMISTRY OF N-(CARBOXYMETHYL) AMINO-ACIDS .1. THE PREPARATION, PROPERTIES, AND CHARACTERIZATION OF N-(CARBOXYMETHYL) AMINO-ACIDS AND THEIR ESTERS
MIYAZAWA, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (09) : 2555 - 2565
[22] SYNTHESIS OF SOME N-LIPOYL AMINO ACIDS AND PEPTIDES
DAIGO, K
BRADY, WT
REED, LJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (04) : 662 - &
[23] ON CARBOXYMETHYL DITHIOPHENYLACETATE AND ITS REACTIONS WITH AMINES, AMINO ACIDS AND PEPTIDES
KJAER, A
ACTA CHEMICA SCANDINAVICA, 1952, 6 (03): : 327 - 332
[24] CONFORMATION OF SIDE GROUPS IN AMINO ACIDS AND PEPTIDES
RAMACHAN.GN
LAKSHMIN.AV
BIOPOLYMERS, 1966, 4 (04) : 495 - &
[25] Building units for N-backbone cyclic peptides .4. Synthesis of protected N-alpha-functionalized alkyl amino acids by reductive alkylation of natural amino acids
Bitan, G
Muller, D
Kasher, R
Gluhov, EV
Gilon, C
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (10): : 1501 - 1510
[26] SYNTHESIS OF N-(CARBOXYMETHYL)BENZYL ESTERS OF BOC-AMINO-ACIDS
KULIKOV, SV
SOKOLOVA, NY
ZHURNAL OBSHCHEI KHIMII, 1992, 62 (10): : 2397 - 2398
[27] AMINO ACIDS AND PEPTIDES .15. SYNTHESIS OF ACTIVE BENZHYDROXAMIC ESTERS OF N-PROTECTED AMINO ACIDS AND PEPTIDES AND THEIR USE FOR SYNTHESIS OF OPTICALLY HOMOGENEOUS PEPTIDES
LUBIEWSK.L
RZESZOTA.B
TASCHNER, E
ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1970, 741 : 157 - &
[28] Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol
Adao, Pedro
Teixeira, Carlos M.
Carvalho, M. Fernanda N. N.
Kuznetsov, Maxim L.
Gomes, Clara S. B.
Pessoa, Joao Costa
MOLECULAR CATALYSIS, 2019, 475
[29] A new approach to Hmb-backbone protection of peptides: Synthesis and reactivity of N-alpha-Fmoc-N-alpha-(Hmb)amino acids
Nicolas, E
Pujades, M
Bacardit, J
Giralt, E
Albericio, F
TETRAHEDRON LETTERS, 1997, 38 (13) : 2317 - 2320
[30] Separation, detection, and quantification of hydroperoxides formed at side-chain and backbone sites on amino acids, peptides, and proteins
Morgan, Philip E.
Pattison, David I.
Hawkins, Clare L.
Davies, Michael J.
FREE RADICAL BIOLOGY AND MEDICINE, 2008, 45 (09) : 1279 - 1289

← 1 2 3 4 5 →