Synthesis of linear gramicidin requires the cooperation of two independent reductases

被引:23
作者
Schracke, N [1 ]
Linne, U [1 ]
Mahlert, C [1 ]
Marahiel, MA [1 ]
机构
[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
关键词
D O I
10.1021/bi050074t
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 linear pentadecapeptide gramicidin has been reported to be assembled by four large multimodular nonribosomal peptide synthetases (NRPSs), LgrABCD, that comprise 16 modules. During biosynthesis, the N-formylated 16mer peptide is bound to the peptidyl carrier protein (PCP) of the terminal module via a thioester bond to the carboxyl group of the last amino acid glycine(16). In a first reaction the peptide is released from the protein template in an NAD(P)H-dependent reduction step catalyzed by the adjacent reductase forming an aldehyde intermediate. Here we present the biochemical proof that this aldehyde intermediate is further reduced by an aldoreductase, LgrE, in an NADPH-dependent manner to form the final product gramicidin A, N-formyl-pentadecapeptide-ethanolamine. To determine the potential use of the two reductases in the construction of hybrid NRPSs, we have tested their ability to accept a variety of different substrates in vitro. The results obtained give way to a broad spectrum of possible use.
引用
收藏
页码:8507 / 8513
页数:7
相关论文
共 33 条
  • [1] Gapped BLAST and PSI-BLAST: a new generation of protein database search programs
    Altschul, SF
    Madden, TL
    Schaffer, AA
    Zhang, JH
    Zhang, Z
    Miller, W
    Lipman, DJ
    [J]. NUCLEIC ACIDS RESEARCH, 1997, 25 (17) : 3389 - 3402
  • [2] Mutational analysis of the C-domain in nonribosomal peptide synthesis
    Bergendahl, V
    Linne, U
    Marahiel, MA
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 2002, 269 (02): : 620 - 629
  • [3] Structural basis for the cyclization of the lipopeptide antibiotic surfactin by the thioesterase domain SrfTE
    Bruner, SD
    Weber, T
    Kohli, RM
    Schwarzer, D
    Marahiel, MA
    Walsh, CT
    Stubbs, MT
    [J]. STRUCTURE, 2002, 10 (03) : 301 - 310
  • [4] In-source fragmentation of peptide aldehydes and acetals:: influence of peptide length and charge state
    Buré, C
    Gobert, W
    Lelièvre, D
    Delmas, A
    [J]. JOURNAL OF MASS SPECTROMETRY, 2001, 36 (10): : 1149 - 1155
  • [5] Lessons from natural molecules
    Clardy, J
    Walsh, C
    [J]. NATURE, 2004, 432 (7019) : 829 - 837
  • [6] Rational design of a bimodular model system for the investigation of heterocyclization in nonribosomal peptide biosynthesis
    Duerfahrt, T
    Eppelmann, K
    Müller, R
    Marahiel, MA
    [J]. CHEMISTRY & BIOLOGY, 2004, 11 (02): : 261 - 271
  • [7] Aminoacyl-SNACs as small-molecule substrates for the condensation domains of nonribosomal peptide synthetases
    Ehmann, DE
    Trauger, JW
    Stachelhaus, T
    Walsh, CT
    [J]. CHEMISTRY & BIOLOGY, 2000, 7 (10): : 765 - 772
  • [8] Lysine biosynthesis in Saccharomyces cerevisiae:: Mechanism of α-aminoadipate reductase (Lys2) involves posttranslational phosphopantetheinylation by Lys5
    Ehmann, DE
    Gehring, AM
    Walsh, CT
    [J]. BIOCHEMISTRY, 1999, 38 (19) : 6171 - 6177
  • [9] Biosynthesis of nonribosomal peptides
    Finking, R
    Marahiel, MA
    [J]. ANNUAL REVIEW OF MICROBIOLOGY, 2004, 58 : 453 - 488
  • [10] Novel insights into siderophore formation in myxobacteria
    Gaitatzis, N
    Kunze, B
    Müller, R
    [J]. CHEMBIOCHEM, 2005, 6 (02) : 365 - 374