Novel peptidomimetic structures: enantioselective synthesis of conformationally constrained lysine, ornithine and alanine analogues from pyroglutamic acid

被引：26

作者：

Goswami, R ^{[1
]}

Moloney, MG ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 23期

关键词：

D O I：

10.1039/a906297a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Conformationally constrained lysine and ornithine analogues, and an L-Ala-L-Ala dipeptide analogue, are available from pyroglutamic acid.

引用

页码：2333 / 2334

页数：2

共 42 条

[1] Torsional and steric effects control the stereoselectivities of alkylations of pyrrolidinone enolates [J].

Ando, K ;

Green, NS ;

Li, Y ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (22) :5334-5335

[2] Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions [J].

Bailey, JH ;

Cherry, DT ;

Crapnell, KM ;

Moloney, MG ;

Shim, SB ;

Bamford, MJ ;

Lamont, RB .

TETRAHEDRON, 1997, 53 (34) :11731-11744

[3] A CONCISE APPROACH TO FUNCTIONALIZED, HOMOCHIRAL PYRROLIDINONES [J].

BAMFORD, MJ ;

BEARD, M ;

CHERRY, DT ;

MOLONEY, MG .

TETRAHEDRON-ASYMMETRY, 1995, 6 (02) :337-340

[4] Functionalised pyrrolidinones derived from (S)-pyroglutamic acid [J].

Beard, MJ ;

Bailey, JH ;

Cherry, DT ;

Moloney, MG ;

Shim, SB ;

Statham, KA ;

Bamford, MJ ;

Lamont, RB .

TETRAHEDRON, 1996, 52 (10) :3719-3740

[5] Alkyl 3-position substituents retard the isomerization of prolyl and hydroxyprolyl amides in water [J].

Beausoleil, E ;

Sharma, R ;

Michnick, SW ;

Lubell, WD .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6572-6578

[6] Asymmetric formation of quaternary centers through aza-annulation of chiral β-enamino amides with acrylate derivatives [J].

Benovsky, P ;

Stephenson, GA ;

Stille, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2493-2500

[7] On the chemoselectivity of pyroglutamates in reactions with indole derivatives [J].

Braña, MF ;

Garranzo, M ;

Pérez-Castells, J .

TETRAHEDRON LETTERS, 1998, 39 (36) :6569-6572

[8] New conformationally constrained Xxx-Pro bicyclic mimetics [J].

Cappelletti, S ;

Pegna, M ;

Zaliani, A ;

Pinori, M .

LETTERS IN PEPTIDE SCIENCE, 1995, 2 (3-4) :161-164

[9] Conjugate addition of nitrogen nucleophiles to an alpha,beta-unsaturated pyrrolidinone [J].

Chan, PWH ;

Cottrell, IF ;

Moloney, MG .

TETRAHEDRON LETTERS, 1997, 38 (33) :5891-5894

[10] A novel method for the formation of 2-azocanones by lactone-to-lactam ring contraction of 2-oxonanones [J].

Derrer, S ;

Feeder, N ;

Teat, SJ ;

Davies, JE ;

Holmes, AB .

TETRAHEDRON LETTERS, 1998, 39 (50) :9309-9312

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