Extended Stokes Shift in Fluorescent Proteins: Chromophore-Protein Interactions in a Near-Infrared TagRFP675 Variant

Kiryl D. Piatkevich, Vladimir N. Malashkevich, Kateryna S. Morozova, Nicolai A. Nemkovich, Steven C. Almo, and Vladislav V. Verkhusha

Supporting Information


10 20 30 40 50 60

EGFP mVskgeelftgvvpilveldgdvnghkfsvsgegegdaty-gkltlkfictt-gklpvpwptL

mPlum MVSKGEENNMAIIKEFMRFKEHMEGSVNGHEFEIEGEGEGRP-YEGTQTARLKVTKGGPLPFAWDIL

mRouge MVSKGEEDNMAIIKEFMRFKTHMEGSVNGHEFEIEGEGEGRP-YEGTQTAKLKVTKGGPLPFAWDIL

E2-Crimson MDSTENVIKPFMRFKVHMEGSVNGHEFEIEGVGEGKP-YEGTQTAKLQVTKGGPLPFAWDIL

mKate MSELIKENMHMKLYMEGTVNNHHFKCTSEGEGKP-YEGTQTMRIKVVEGGPLPFAFDIL

GmKate MSELIKENMHMKLYMEGTVNNHHFKCTSEGEGKP-YEGTQTMRIKVVEGGPLPFAFDIL

mNeptune MVSKGEELIKENMHMKLYMEGTVNNHHFKCTSEGEGKP-YEGTQTGRIKVVEGGPLPFAFDIL

eqFP650 MGEDSELISENMHMKLYMEGTVNGHHFKCTSEGEGKP-YEGTQTAKIKVVEGGPLPFAFDIL

eqFP670 MGEDSELISENMHTKLYMEGTVNGHHFKCTSEGEGKP-YEGTQTCKIKVVEGGPLPFAFDIL

TagRFP657 MSELITENMHMKLYMEGTVNNHHFKCTSEGEGKP-YEGTQTQRIKVVEGGPLPFAFDIL

TagRFP675 MSELIKENMHMKLYMEGTVNNHHFKCTSEGEGKP-YEGTQTQRIKVVEGGPLPFAFDIL

70 80 90 100 110 120

EGFP vttfTygvqcfsrypdhmkqhdffksampegyvqertiffkddgnyktraevkfeGDtLV

mPlum SPQIQYGSKAYVKHPADIP--DYLKLSFPEGFKWERVMNFEDGGVVTVTQDSSLQDGEFI

mRouge SPQFQYGSKAYVKHPADIP--DYLKLSFPEGFKWERVMNFEDGGVVTVTQDSSLQDGEFI

E2-Crimson SPQFFYGSKAYIKHPADIP--DYLKQSFPEGFKWERVMNFEDGGVVTVTQDSSLQDGTLI

mKate ATSFMYGSKTFINHTQGIP--DFFKQSFPEGFTWERVTTYEDGGVLTATQDTSLQDGCLI

GmKate ATSFMYGSKTFINHTQGIP--DFFKQSFPEGFTWERVTTYEDGGVLTATQDTSLQDGCLI

mNeptune ATCFMYGSKTFINHTQGIP--DFFKQSFPEGFTWERVTTYEDGGVLTATQDTSLQDGCLI

eqFP650 ATSFMYGSKTFINHTQGIP--DFFKQSFPEGFTWERITTYEDGGVLTATQDTSLQNGCLI

eqFP670 ATSFMYGSKTFINHTQGIP--DFFKQSFPEGFTWERITTYEDGGVLTATQDTSLQNGCLI

TagRFP657 ATSFMYGSHTFINHTQGIP--DFWKQSFPEGFTWERVTTYEDGGVLTATQDTSLQDGCLI

TagRFP675 ATSFMYGSKTFINHTQGIP--DFWKQSFPEGFTWERVTTYEDGGVLTATQDTSLQDGCLI

- 130 140 150 160 170 180

EGFP nrielkgidfkedgnilghkleynynshnvyimadkqkngikvnfkirhniedgSVQLad

mPlum YKVKVRGTNFPSDGPVMQKKTMG-WEASTERMYPE--DGALKGEMKMRLRLKDGGHYDAE

mRouge YKVKLRGTNFPSDGPVMQKKTMG-WEACSERMYPE--DGALKGEMKMRLKLKDGGHYDAE

E2-Crimson YHVKFIGVNFPSDGPVMQKKTLG-WEPSTERNYPR--DGVLKGENHMALKLKGGGHYLCE

mKate YNVKIRGVNFPSNGPVMQKKTLG-WEASTEMLYPA--DGGLEGRSDMALKLVGGGHLICN

GmKate YNVKIRGVNFPSNGPVMQKKTLG-WEACTEMLYPA--DGGLEGRADMALKLVGGGHLICN

mNeptune YNVKIRGVNFPSNGPVMQKKTLG-WEASTETLYPA--DGGLEGRCDMALKLVGGGHLICN

eqFP650 YNVKINGVNFPSNGPVMQKKTLG-WEASTEMLYPA--DSGLRGHSQMALKLVGGGYLHCS

eqFP670 YNVKINGVNFPSNGPVMQKKTLG-WEANTEMLYPA--DSGLRGHNQMALKLVGGGYLHCS

TagRFP657 YNVKIRGVNFPSNGPVMQKKTLG-WEAHTEMLYPA--DGGLEGRTALALKLVGGGHLICN

TagRFP675 YNVKIRGVNFPSNGPVMQKKTLG-WEANTEMMYPA--DGGLEGRNYMALKLVGGGHLICS

190 200 210 220 230

EGFP hyqqntpigd-gpvllpdnhylstqsalskdpnekrdhmvllefvtaagithgmdelyk

mPlum VKTTYMAKKP---VQLPGAYKTDIKLDITSH-NEDYTIVEQYERAEGRHSTggmdelyk

mRouge VKTTYKAKKP---VQLPGAYNTNTKLDITSH-NEDYTIVEQYERNEGRHSTGGMDELYK

E2-Crimson FKSIYMAKKP---VKLPGYHYVDYKLDITSH-NEDYTVVEQYERAEARHHLFQ

mKate LKTTYRSKKPAKNLKMPGVYYVDRRLERIKE-ADKETYVEQHEVAVARYCDLPSKLGHK

GmKate LKTTYRSKKPAKNLKMPGVYYVDRRLERIKE-ADKETYVEQHEVAVARYCDLPSKLGHK

mNeptune LKTTYRSKKPAKNLKMPGVYFVDRRLERIKE-ADNETYVEQHEVAVARYCDLPSKLGHKLN

eqFP650 LKTTYRSKKPAKNLKMPGFYFVDRKLERIKE-ADKETYVEQHEMAVARYCDLPSKLGHS

eqFP670 LKTTYRSKKPAKNLKMPGFYFVDRKLERIKE-ADKETYVEQHEMAVARYCDLPSKLGHS

TagRFP657 FKTTYRSKKPAKNLKMPGVYYVDYRLERIKE-ADKETYVEQHEVAVARYCDLPSKLGHKLN

TagRFP675 LKTTYRSKKPAKNLKMPGVYYVDRRLERIKE-ADKETYVEQHEVAVARYCDLPSKLGHKLN

Supporting Figure 1. Alignment of the amino acid sequences for TagRFP675, far-red FPs, and EGFP. Internal amino acids are highlighted in gray. The chromophore-forming residues are underlined. Mutations resulting in the conversion of mKate into TagRFP675 are shown in red. The residues highlighted in green are suggested being responsible for the bathochromic shift of emission in the respective FPs. The alignment numbering follows that for EGFP.

Supporting Figure 2. Molecular structure of the chromophore superimposed onto the refined 2Fo-Fc electron density. (A) A subunit, pH 8.0. The chromophore adopts predominantly cis-configuration. (B) B subunit B, pH 8.0. The chromophore adopts cis-configuration (occupancy 0.6) and trans-configuration (occupancy 0.4). (C) A subunit, pH 4.5. The chromophore adopts predominantly cis-configuration. (D) B subunit, pH 4.5. The chromophore adopts cis-configuration (occupancy 0.5) and trans-configuration (occupancy 0.5). The occupancy of cis- and trans-chromophore was calculated during structure refinement.

Supporting Figure 3. Emission spectra of TagRFP675 at pH 4.5. (A) Emission spectrum at 460 nm excitation. (B) Emission spectrum at 570 nm excitation.


Supporting Figure 4. Instantaneous fluorescence spectra of (A) TagRFP675, (B) TagRFP675/Q41M, (C) TagRFP675/Q41P, (D) TagRFP675/N143S, (E) TagRFP675/N158K, and (F) mKate measured at different registration times, indicated at each plot. The measurements were performed at 298 K with excitation wavelength 337.1 nm. The arrows indicate maximum of fluorescence emission, λ, wavelength, and τ, fluorescence life-time.


Supporting Figure 5. Emission spectra of TagRFP675, TagRFP675/Q41M, TagRFP675/Q41P and mKate at different temperatures. (A) Emission of TagRFP765 at 298K (red line), 196K (cyan line) and 77K (blue line). (B) Emission of TagRFP765/Q41M at 298K (red line), 196K (cyan line) and 77K (blue line). (C) Emission of TagRFP765/Q41P at 298K (red line), 196K (cyan line) and 77K (blue line). (D) Emission of mKate at 298K (red line), 196K (cyan line) and 77K (blue line).


Supporting Figure 6. Emission spectra of TagRFP675 at various excitation wavelengths at room temperature.


Supporting Table 1. Data collection and refinement statistics.

TagRFP675 (pH 4.5) TagRFP675 (pH 8.0)

Data collection

Beamline NSLS-X29A NSLS-X29A

Wavelength (Å) 1.08 1.08

Resolution limits (Å) 20–2.30 20–2.30

Observed reflections 692565 557113

Unique reflections 32982 35919

Completeness (%) 99.5 (100.0)a 99.2 (100.0)a

Rmergeb 0.090 (0.660)a 0.074 (0.740)a

Refinement statistics

Protein non-hydrogen atoms 3643 3604

Water molecules 243 169

Rcrystc 0.188 (0.208)a 0.191 (0.189)a

Rfreec 0.232 (0.259)a 0.233 (0.261)a

Average B-factor (Å2) 40.5 34.2

RMSD from ideality

Bond length, Å 0.008 0.009

Bond angles (°) 1.55 1.66

Torsion angles (°) 24.2 25.6

Ramachandran plot

Core (%) 98.1 98.1

Allowed (%) 1.6 1.6

Generous (%) 0.3 0.3

a Values in parentheses indicate statistics for the high resolution bin. b Rmerge = SS j|Ij(hkl) – <I(hkl)>|/ SS j|<I(hkl)>|, where Ij is the intensity measurement for reflection j and <I> is the mean intensity over j reflections. c Rcryst/(Rfree) = S ||Fo(hkl)| – |Fc(hkl)||/ S |Fo(hkl)|, where Fo and Fc are observed and calculated structure factors, respectively. No s-cutoff was applied. 5% of the reflections were excluded from refinement and used to calculate Rfree.

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