Synthesis of (S)- and (R)-5-Oxo-piperazine-2-Carboxylic Acid and Its Application to Peptidomimetics

被引：10

作者：

Guitot, Karine ^{[1
,2
]}

Carboni, Stefano ^{[2
]}

Reiser, Oliver ^{[1
]}

Piarulli, Umberto ^{[2
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

[2] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; PIPECOLIC ACID; ASYMMETRIC-SYNTHESIS; PEPTIDE-BONDS; DERIVATIVES; ENANTIOMERS; RESOLUTION; ANALOGS; MODEL;

D O I：

10.1021/jo901389q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward synthesis of (S)- and (R)-N-Boc-5-oxopiperazine-2-carboxylic acid is reported starting from L- or D-serine and ethyl glyoxylate. Those were evaluated as constituents in two tetrapeptides by studying their secondary Structure by H-1 NMR spectroscopy. In the case of Boc-Val-(S)-PCA-Gly-Leu-OMe, two readily interconverting conformations (in a 40%: 60% ratio) were observed, differing for the cis-trans isomerizaton of the tertiary amide bond, while Boc-Val-(R)-PCA-Gly-Lcu-OMe displayed an equilibrium between a gamma-turn and it type II beta-turn conformation.

引用

页码：8433 / 8436

页数：4

共 50 条

[31] Application of the Ugi reaction with multiple amino acid-derived components: synthesis and conformational evaluation of piperazine-based minimalist peptidomimetics
Stucchi, Mattia
Cairati, Silvia
Cetin-Atalay, Rengul
Christodoulou, Michael S.
Grazioso, Giovanni
Pescitelli, Gennaro
Silvani, Alessandra
Yildirim, Deniz Cansen
Lesma, Giordano
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (17) : 4993 - 5005
[32] A convenient synthesis of 5-fluorofuran-2-carboxylic acid
Song, Renhua
Lin, Weimin
Jiang, Qin
TETRAHEDRON LETTERS, 2011, 52 (38) : 4965 - 4966
[33] AN IMPROVED SYNTHESIS OF 5-METHYLPYRAZINE-2-CARBOXYLIC ACID
IOVEL, I
GOLDBERG, Y
SHYMANSKA, M
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (02) : 188 - 190
[34] An improved synthesis of 5-fluorothiophene-2-carboxylic acid
Chambers, RJ
Marfat, A
SYNTHETIC COMMUNICATIONS, 2000, 30 (19) : 3629 - 3632
[35] SYNTHESIS OF R,S-3-QUINUCLIDINYL ESTERS OF QUINUCLIDINE-2-CARBOXYLIC AND QUINUCLIDINE-3-CARBOXYLIC ACID
BINIECKI, S
CISZEWSKI, L
ACTA POLONIAE PHARMACEUTICA, 1981, 38 (02): : 167 - 170
[36] PRODUCTS FORMED IN THE RADIATION SYNTHESIS OF 5-OXO-TETRAHYDROFURAN-3-CARBOXYLIC ACID-DERIVATIVES
KUCERA, J
MORAVEC, J
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1980, 45 (12) : 3564 - 3570
[37] Synthesis and Biological Evaluation of Novel 5-Oxo-1-Phenylpyrrolidine-3-Carboxylic Acid Analogs
Devi, Poornima
Bishnoi, Abha
Srivastava, Krishna
Kumar, Sunil
Srivastava, Ankita
Fatma, Shaheen
DRUG RESEARCH, 2019, 69 (05) : 271 - 276
[38] Synthesis of 5-oxo-1-(5-R-1,3,4-thiadiazol-2-yl)pyrrolidine-3-carboxylic acids
Serkov, S. A.
Sigay, N. V.
Kostikova, N. N.
Tyurin, A. P.
Kolotyrkina, N. G.
Gazieva, G. A.
RUSSIAN CHEMICAL BULLETIN, 2023, 72 (08) : 1837 - 1843
[39] Synthesis of 5-oxo-1-(5-R-1,3,4-thiadiazol-2-yl)pyrrolidine-3-carboxylic acids
S. A. Serkov
N. V. Sigay
N. N. Kostikova
A. P. Tyurin
N. G. Kolotyrkina
G. A. Gazieva
Russian Chemical Bulletin, 2023, 72 : 1837 - 1843
[40] An improved synthesis of (S)-(+)- and (R)-(-)-[2.2]paracyclophane-4-carboxylic acid
Tetrahedron Asymmetry, 4 (653):

← 1 2 3 4 5 →