The sequence of an isonitrile synthase, isnA, was used to search fully sequenced bacterial genomes as well as DNA extracted directly from environmental samples for operons that might use isnA homologues in the biosynthesis of new natural products. This manuscript describes the biosynthetic operons that were found and the compounds that were produced from the heterologous expression of these operons. The identification of new metabolites from the expression of this family of operons suggests that the activation of even simple, sequenced natural product biosynthetic gene clusters using standard E. coli protein expression vectors will be a rewarding and straightforward strategy for the discovery of structurally novel metabolites

DNA modification, metabolites, biosynthetic operons

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
4	aLRhap	99.2	71.5	72.2	73.4	70.4	18.2
	Subst	158.6	117.6	129.3	127.6	129.3	117.6	136.9	110.5	166.2


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
4	aLRhap	5.53	4.04	3.85	3.51	3.60	1.18
	Subst	-	7.10	7.49	-	7.49	7.10	7.05	6.62	-


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
4	aLRhap	99.2/5.53	71.5/4.04	72.2/3.85	73.4/3.51	70.4/3.60	18.2/1.18
	Subst		117.6/7.10	129.3/7.49		129.3/7.49	117.6/7.10	136.9/7.05	110.5/6.62	

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

[C-]#[N+]/C=C/c1ccc(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)cc1

291.303 g/mol (C₁₅H₁₇NO₅)