Chemoenzymatic synthesis of polypeptides containing the unnatural amino acid 2-aminoisobutyric acid

被引：40

作者：

Tsuchiya, Kousuke ^{[1
]}

Numata, Keiji ^{[1
]}

机构：

[1] RIKEN Ctr Sustainable Resource Sci, Enzyme Res Team, Biomass Engn Res Div, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 53期

关键词：

DIETHYL ESTER; SECONDARY STRUCTURE; CATALYZED SYNTHESIS; PEPTIDES; PAPAIN; ALPHA; COPOLYMERIZATION; OLIGOMERIZATION; OLIGOPEPTIDES; INITIATOR;

D O I：

10.1039/c7cc03095a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Polypeptides containing 2-aminoisobutyric acid (Aib) units as an unnatural amino acid residue were synthesized by papain-catalyzed chemoenzymatic polymerization of a tripeptide ethyl ester L-Ala-Aib-L-Ala-OEt in an aqueous medium. The Aib-containing polypeptide adopted an alpha-helix conformation in both the solid and solution phases, which was induced by the periodic Aib residue.

引用

页码：7318 / 7321

页数：4

共 37 条

[1] Proteinase K-Catalyzed Synthesis of Linear and Star Oligo(L-phenylalanine) Conjugates [J].

Ageitos, Jose M. ;

Baker, Peter J. ;

Sugahara, Michihiro ;

Numata, Keiji .

BIOMACROMOLECULES, 2013, 14 (10) :3635-3642

[2] The Benzyl Ester Group of Amino Acid Monomers Enhances Substrate Affinity and Broadens the Substrate Specificity of the Enzyme Catalyst in Chemoenzymatic Copolymerization [J].

Ageitos, Jose Manuel ;

Yazawa, Kenjiro ;

Tateishi, Ayaka ;

Tsuchiya, Kousuke ;

Numata, Keiji .

BIOMACROMOLECULES, 2016, 17 (01) :314-323

[3] The Pharmacological Potential of Non-ribosomal Peptides from Marine Sponge and Tunicates [J].

Agrawal, Shivankar ;

Adholeya, Alok ;

Deshmukh, Sunil K. .

FRONTIERS IN PHARMACOLOGY, 2016, 7

[4]

ARGOS P, 1986, METHOD ENZYMOL, V130, P185

[5] Chemoenzymatic Synthesis of Poly(L-alanine) in Aqueous Environment [J].

Baker, Peter James ;

Numata, Keiji .

BIOMACROMOLECULES, 2012, 13 (04) :947-951

[6]

COMBES D, 1992, ANN NY ACAD SCI, V672, P409

[7] Screw-Sense Control of Helical Oligopeptides Containing Equal Amounts of L- and D-Amino Acids [J].

Demizu, Yosuke ;

Doi, Mitsunobu ;

Sato, Yukiko ;

Tanaka, Masakazu ;

Okuda, Haruhiro ;

Kurihara, Masaaki .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (40) :11107-11109

[8] Short One-Pot Chemo-Enzymatic Synthesis of L-Lysine and L-Alanine Diblock Co-Oligopeptides [J].

Fagerland, Jenny ;

Finne-Wistrand, Anna ;

Numata, Keiji .

BIOMACROMOLECULES, 2014, 15 (03) :735-743

[9] Effect of the electric field generated by the helix dipole on photoinduced intramolecular electron transfer in dichromophoric alpha-helical peptides [J].

Galoppini, E ;

Fox, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) :2299-2300

[10] Translation Initiation with Initiator tRNA Charged with Exotic Peptides [J].

Goto, Yuki ;

Suga, Hiroaki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (14) :5040-+

← 1 2 3 4 →