a-d, Fluorescence from cells containing O1-strepGFP(40XXXX)His6, with XXXX being the codon at position 40 in sfGFP: TAGA, CTAG, AGGA or AGTA. E. coli also contained O-riboQ1 and the aaRS and tRNA operons (aaRS4_1-2/tRNA4(quad)); these operons expressed MmPylRS/MspetRNAPyl-evolUCUA, MrumPylRS(NmH)/MinttRNAPyl-A17VC10UCCU, AfTyrRS(PheI)/AftRNATyr-A01CUAG and Mg1PylRS(CbzK)/MalvtRNAPyl-8UACU. The indicated ncAAs: Nπ-methyl-L-histidine (NmH) 2, N6-((benzyloxy)carbonyl)-L-lysine (CbzK) 3, N6-((allyloxy)carbonyl)-L-lysine (AllocK) 4, (S)-2-amino-3-(4-iodophenyl)propanoic acid (PheI) 5 were added to cells or omitted (-). Each codon was only efficiently decoded in the presence of cognate ncAA of the aaRS/tRNA pair assigned to the respective quadruplet codon: (a) O1-strepGFP(40TAGA)His6 decoded by MmPylRS/MspetRNAPyl-evolUCUA, (b) O1-strepGFP(40AGGA)His6 decoded by MrumPylRS(NMH)/MinttRNAPyl-A17VC10UCCU, (c) O1-strepGFP(40AGTA)His6 decoded by Mg1PylRS(CbzK)/ MalvtRNAPyl-8UACU, and (d) O1-strepGFP(40CTAG)His6 decoded by AfTyrRS(PheI)/AftRNATyr-A01CUAG. Each bar represents the mean of three biological replicates ± s.d. The individual data points are shown as dots. e-h, Positive electrospray TOF-MS of nickel-NTA-purified strepGFPHis6, expressed from O1-strepGFP(40XXXX)His6, with XXXX being either TAGA (e), AGGA (f), AGTA (g) or CTAG (h), in the presence of NmH 2, CbzK 3, AllocK 4, PheI 5. Cells also contained O-riboQ1 and operon aaRS4_2-1/tRNA4(quad). strepGFP(40AllocK)His6: mass predicted 29113.2, mass found 29114.8. strepGFP(40NmH)His6: mass predicted 29052.1, mass found 29052.5. strepGFP(40CbzK)His6: mass predicted 29163.3, mass found 29164.2. strepGFP(40PheI)His6: mass predicted 29174.03, mass found 29174.2. The experiment was performed three times with similar results.