Nogl_00190 Nogl_00190   Nogl_00210 Nogl_00210

Nogl_00200 : CDS information

close this sectionLocation

Organism
StrainATCC 27451 (=NBRC 13445)
Entry nameNogalamycin
Contig
Start / Stop / Direction20,196 / 19,762 / - [in whole cluster]
7,559 / 7,125 / - [in contig]
Locationcomplement(19762..20196) [in whole cluster]
complement(7125..7559) [in contig]
TypeCDS
Length435 bp (144 aa)
Click on the icon to see Genetic map.

close this sectionAnnotation

Category3.4 other modification
Productnogalonic acid methyl ester cyclase
Product (GenBank)nogalonic acid methyl ester cyclase
Gene
Gene (GenBank)snoaL
EC number
Keyword
  • 4th ring
  • C-9 S-stereochemistry
Note
  • The N-terminal position was modified from original INSDC entry.
Note (GenBank)
Reference
ACC
PmId
[10639368] Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater. (Antimicrob Agents Chemother. , 2000)
[15071504] Structure of the polyketide cyclase SnoaL reveals a novel mechanism for enzymatic aldol condensation. (EMBO J. , 2004)
[16414075] Crystal structure of the polyketide cyclase AknH with bound substrate and product analogue: implications for catalytic mechanism and product stereoselectivity. (J Mol Biol. , 2006)
comment
[PMID: 10639368](2000)
aknH(acmA)の実験[PMID: 10658662]の改変。
AknH = aklanonic acid methyl ester(AAME) → aklaviketone

pSY15bのS.lividans TK24導入でauramycinoneを産生。
pSY15bのacmA→snoaLに置換したpSY15dでは9-epi-auramycinone(nogalamycinone)を産生。
よってnogalamycinに見られる珍しい9S立体配置はSnoaLのみに由来する。

pSY15d = snogF + snoaEDCB + snorA + snoa123 + snoaL + dauE
7-ketoreductase_dauEがあるのでnogalaviketone→nogalamycinoneが検出されている。

よってSnoaLは、nogalamycin生合成における
nogalonic acid methyl ester(NAME)→nogalaviketone(9-epi-auraviketone)
への4環目の閉環を担い、9S配置をもたらすcyclase.

--
[PMID: 15071504](2004)
SnoaLの結晶構造解析とsite-directed mutagenesis実験。
SnoaLによって触媒される分子内aldol縮合のメカニズムは、古典的なaldolasesのメカニズムと異なる。

--
[PMID: 16414075](2006) abstract
AknHとSnoaLは構造的、機構的に似ているが、反応産物が立体化学的に異なる。
同じ基質(NAME)を与えたとき、AknH産物は一般的なC9-R、SnoaL産物はC9-S。
これはAknHのTyr15 and Asn51に由来し、SnoaLのPhe and Leuで置換すると産物立体選択性は失われる。

close this sectionSequence

selected fasta
>nogalonic acid methyl ester cyclase [nogalonic acid methyl ester cyclase]
MSRQTEIVRRMVSAFNTGRTDDVDEYIHPDYLNPATLEHGIHTGPKAFAQLVGWVRATFS
EEARLEEVRIEERGPWVKAYLVLYGRHVGRLVGMPPTDRRFSGEQVHLMRIVDGKIRDHR
DWPDFQGTLRQLGDPWPDDEGWRP
selected fasta
>nogalonic acid methyl ester cyclase [nogalonic acid methyl ester cyclase]
TTGAGCCGTCAGACAGAGATCGTCCGCCGGATGGTGAGCGCCTTCAACACCGGCAGGACC
GACGACGTGGACGAGTACATCCACCCCGACTACCTCAATCCGGCCACCTTGGAACACGGC
ATCCACACCGGGCCCAAGGCGTTCGCCCAGCTGGTCGGCTGGGTGCGGGCGACGTTCTCC
GAGGAAGCCCGCCTGGAGGAGGTGCGGATCGAGGAGCGCGGCCCGTGGGTCAAGGCCTAC
CTCGTGCTCTACGGCCGCCACGTCGGCCGGCTTGTCGGTATGCCGCCCACCGACCGGCGC
TTCTCCGGTGAACAGGTGCACCTGATGCGCATCGTCGACGGGAAGATCCGCGACCACCGG
GACTGGCCCGACTTCCAGGGGACGCTGCGCCAGCTCGGCGACCCGTGGCCCGACGACGAG
GGCTGGCGTCCGTGA

close this sectionFeature

BLASTP
Database:UniProtKB:2011_09 		show BLAST table
InterPro
Database:interpro:38.0
IPR009959 Polyketide cyclase SnoaL-like domain (Domain)
[6-132] 5.7e-31 PF07366
PF07366   SnoaL
SignalP No significant hit
TMHMM No significant hit
Nogl_00190 Nogl_00190   Nogl_00210 Nogl_00210
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