I am willing to bet that the ketone is covalently reacting with the
arginine and the result is what you see :)

Artem

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On Thu, Nov 7, 2019 at 3:33 AM <[email protected]> wrote:

> Dear HK,
>
> In your case mass spec would be extremely valuable. Not only could it
> prove or rule out a covalent link, it will also convince referees that the
> link is real.
> There is clearly more density than the degraded product you showed. I
> would also ask an experienced chemist if a link between your ligand and the
> arginine would be possible. Finally, I would also do a quality check on the
> ligand you used. Might it be that some reactive intermediate from the
> synthesis still is present?
>
> Best,
> Herman
>
> -----Ursprüngliche Nachricht-----
> Von: [email protected] <[email protected]>
> Gesendet: Donnerstag, 7. November 2019 07:58
> An: Schreuder, Herman /DE <[email protected]>
> Cc: [email protected]
> Betreff: [EXTERNAL] Re: [ccp4bb] Occupancy refinement of overlapping
> electron density of a residue and ligand
>
> EXTERNAL : Real sender is  [email protected]
>
>
>
> Hi Herman,
>
> Thanks for the suggestion. In principle, I have refined the structure
> without Arg and ligand, as well as the connected residues to the Arg.
> However, I still see the connected density of Arg and the ligand (Figure -
> unmodel1.png - only removal of Arg and ligand).
>
> I have tried to refine the degraded product but the positive density in
> between Arg and the ligand is still there, indicating something should be
> modeled there (Figure - degraded_product.png and degraded_product2.png -
> both figures are the same ligand but with different side view).
>
> I also tried to model the ligand in different conformation but still the
> same as shown in degraded product. The positive density is there between
> Arg and the ligand.
>
> For both cases, I refined Arg with full occupancy but ligand with
> occupancy refinement. Now, Arg did not flip away from the density.
>
> I might have a look at the mass-spec to check whether it is covalently
> linked although I am not aware of the reactivity of the moiety of the
> ligand and we never see this compound to covalent link with protein in our
> experience.
>
> Thanks for the advice and suggestion. It is very helpful.
>
> Thanks.
>
> Best
> HK
>
>
>
> Quoting [email protected]:
>
> > Hi Heng-Keat,
> >
> > I had again a look at your electron density pictures and these were my
> > impressions:
> > 1) the Arginine as fitted looks fully occupied. There are no hints for
> > an alternative conformations.
> > 2) The fit of the ligand, although reasonable, is not extremely good.
> >
> > It seems that the only reason to invoke partial occupancies for the
> > Arginine and ligand are problems to fit both the ligand and the
> > arginine in the available density. This means that for the overlapping
> > parts, to sum of the occupancies is maximal 1.0.
> > However, the ligand and the Arginine do not look half occupied.
> >
> > So I would look at other explanations:
> > - would it be possible that the ligand reacts covalently with the
> > Arginine? The density looks pretty continuous to me.
> > - could it be that instead of the intended ligand, some side- or
> > degradation product has bound?
> >
> > What I would also do, but what you probably already did, is to delete
> > the ligand and the Arginine side chain atoms and run several rounds of
> > refinement, to get an electron density map with as much bias as
> > possible removed.
> >
> > Good luck!
> > Herman
> >
> > -----Original Message-----
> > From: CCP4 bulletin board <[email protected]> On Behalf Of
> > Heng-Keat Tam
> > Sent: Mittwoch, 6. November 2019 07:30
> > To: [email protected]
> > Subject: [EXTERNAL] Re: [ccp4bb] Occupancy refinement of overlapping
> > electron density of a residue and ligand
> >
> > EXTERNAL : Real sender is  [email protected]
> >
> >
> >
> > Hi Nestor,
> >
> > I think the reason for Arg side chain to curl up is because I refined
> > ligand and Arg side chain with occupancy refinement, and the Arg moved
> > away from the density, most likely due to 'repulsion' from ligand.
> >
> > The other question is: Is it possible that the H-bonds stay very
> > close? As I tried to 'real space refine' in coot, and the Arg side
> > chain flipped away from the density.
> >
> > Thanks for the suggestion.
> >
> > Best
> > HK
> >
> >
> > Quoting Nestor Concha <[email protected]>:
> >
> >> Hi Tam,
> >> The density looks very strong and therefore I'm going to guess that
> >> the Arg guanidimium stays in contact/interacts with the ligand and
> >> with the phosphate/sulfate next to it. Perhaps it is one of those
> >> close interactions with shorter H-bonds that usual given the
> >> arrangement of ligand-phosphate/sulfate-Arg.  I'd try to find a
> >> rotamer for the Arg that leaves the interactions intact rather than
> >> refine occupancies. Seems that the Arg side chain is curled up ????
> >> Nestor
> >>
> >> -----Original Message-----
> >> From: CCP4 bulletin board <[email protected]> On Behalf Of
> >> Heng-Keat Tam
> >> Sent: Tuesday, November 5, 2019 10:55 AM
> >> To: [email protected]
> >> Subject: Re: [ccp4bb] Occupancy refinement of overlapping electron
> >> density of a residue and ligand
> >>
> >> EXTERNAL
> >>
> >> Dear Rob,
> >>
> >> I would like to model the alternative position for the side chain of
> >> R120 but I don't really know whether the alternative conformation
> >> exist as shown in the attached figure - density without the ligand
> >> and
> >> R120 overlaid with the refined structures of modeled ligand and R120.
> >> The ligand was modeled in two different conformations. From the
> >> density, it seems to me that the density is connected or overlapped.
> >>
> >> It should not be a post-translation modification as it is well-known
> >> that there is no post-translation modification for this protein.
> >> Furthermore, the crystal was obtained by co-crystallization of
> >> protein with the ligand itself. The density seems to be the expected
> ligand.
> >>
> >> Thanks for the advice.
> >>
> >> Best regards
> >> HK
> >>
> >>
> >> Quoting Robert Nicholls <[email protected]>:
> >>
> >>> Dear HK,
> >>>
> >>> No that's not quite correct - 'occupancy group alts complete' means
> >>> that both R120 and the ligand are constrained so that their
> >>> occupancies sum to unity. In contrast, 'occupancy group alts
> >>> incomplete' means that the occupancies of R120 and the ligand will
> >>> not be constrained to sum to unity (but the sum of their occupancies
> >>> must be less than one). In both cases, R120 and the ligand will "see"
> >>> each other in a certain sense. But, because they are assigned to
> >>> different groups, it is assumed that they are present in different
> >>> parts of the crystal. This means that they can overlap.
> >>>
> >>> Assuming that the ligand is in the correct conformation, I suspect
> >>> the source of your problem is that you are modelling the side chain
> >>> of
> >>> R120 as only one conformation. And I would also include the other
> >>> atoms in the side chain - CB and CG.
> >>>
> >>> If you are modelling the sidechain of R120 with partial occupancies,
> >>> then you should model those side chain atoms in two alternative
> >>> positions (i.e. representing the portions of the crystal that
> >>> do/don't have the ligand bound). This will help to ensure that your
> >>> model makes physical sense. So the ligand plus the alt of R120 in
> >>> the portion of the crystal that contains the ligand would be
> >>> assigned to one occupancy group, and the alt of R120 in the portion
> >>> of the crystal that does not contain the ligand would be assigned to
> >>> the second group. In this case it would be appropriate to specify
> >>> 'occupancy group alts complete', because the occupancies for the two
> >>> alternative conformers of R120 should sum to unity. Although no
> >>> doubt the estimation of the occupancies would be dominated by the
> >>> ligand in this case.
> >>>
> >>> Be sure to check your B-factors after occupancy refinement to make
> >>> sure the whole picture makes sense. Assuming your current model is
> >>> essentially correct, from visual inspection it looks like R120 will
> >>> have low occupancy and low B-factors when the ligand is not present
> >>> (or at least B-factors consistent with the environment), but will
> >>> have high occupancy and high B-factors when the ligand is present.
> >>>
> >>> On another note, have you considered whether that part of the ligand
> >>> could be modelled in a slightly different conformation, or whether
> >>> there could be a post-translation modification?
> >>>
> >>> I hope that helps,
> >>> Rob
> >>>
> >>>
> >>> Dr Rob Nicholls
> >>> Senior Investigator Scientist
> >>> MRC Laboratory of Molecular Biology
> >>> Francis Crick Avenue
> >>> Cambridge Biomedical Campus
> >>> Cambridge CB2 0QH
> >>>
> >>>
> >>>
> >>>> On 5 Nov 2019, at 13:36, HK <[email protected]> wrote:
> >>>>
> >>>> Dear all,
> >>>>
> >>>> I have problem with occupancy refinement by Refmac5 for an
> >>>> overlapping electron density of part of residue (an arginine) and
> >>>> part of ligand (tetracyclic compound) (attached figures in Dropbox
> >>>> with a link as shown below).
> >>>>
> >>>> https://urldefense.proofpoint.com/v2/url?u=https-3A__www.dropbox.co
> >>>> m
> >>>> _sh_ppmfp5dnpy1b9e9_AAAV79bOzPHQUrVYp9loMwyha-3F&d=DwIBaQ&c=Dbf9zos
> >>>> w
> >>>> cQ-CRvvI7VX5j3HvibIuT3ZiarcKl5qtMPo&r=HK-CY_tL8CLLA93vdywyu3qI70R4H
> >>>> 8
> >>>> oHzZyRHMQu1AQ&m=EoLwt0JuWdDOc1BU6xjU4le8GxWW0NB5xhp-20uHVws&s=gY91r
> >>>> A 7hskyc0OM1awqWwiv2ufjEmlQN1QyqosE8YQQ&e=
> >>>> dl=0
> >>>>
> >>>> I refined part of the side chain of residue 120 and ligand (chain J
> >>>> residue 1105) with Refmac keyword as shown below. Unfortunately,
> >>>> the side chain of arginine moves away from the density but the
> >>>> ligand stays in the density. As far as I understood, occupancy
> >>>> refinement with keyword 'occupancy group alts complete' means both
> >>>> R120 and the ligand do not meet each other.  Did I miss something
> >>>> from the occupancy refinement keyword?
> >>>>
> >>>> occupancy group id 1 chain A residue 120 atom NE occupancy group id
> >>>> 1 chain A residue 120 atom CZ occupancy group id 1 chain A residue
> >>>> 120 atom NH2 occupancy group id 1 chain A residue 120 atom NH1
> >>>> occupancy group id 1 chain A residue 120 atom CD occupancy group id
> >>>> 2 chain J residue 1105 occupancy group alts complete 1 2 occupancy
> >>>> refine
> >>>>
> >>>> Thank you for the advice.
> >>>>
> >>>> Best regards
> >>>> HK
> >>>>
> >>>> ###################################################################
> >>>> #
> >>>> #
> >>>> ###
> >>>>
> >>>> To unsubscribe from the CCP4BB list, click the following link:
> >>>> https://urldefense.proofpoint.com/v2/url?u=https-3A__www.jiscmail.a
> >>>> c
> >>>> .uk_cgi-2Dbin_webadmin-3FSUBED1-3DCCP4BB-26A-3D1&d=DwIBaQ&c=Dbf9zos
> >>>> w
> >>>> cQ-CRvvI7VX5j3HvibIuT3ZiarcKl5qtMPo&r=HK-CY_tL8CLLA93vdywyu3qI70R4H
> >>>> 8
> >>>> oHzZyRHMQu1AQ&m=EoLwt0JuWdDOc1BU6xjU4le8GxWW0NB5xhp-20uHVws&s=C6m6f
> >>>> Y EOPl79xkEzUw4GMTCpsV1JmEBJmKwXr5Gk4CQ&e=
> >>>
> >>>
> >>> ####################################################################
> >>> #
> >>> #
> >>> ##
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> >>> Q
> >>> -CRvvI7VX5j3HvibIuT3ZiarcKl5qtMPo&r=HK-CY_tL8CLLA93vdywyu3qI70R4H8oH
> >>> z
> >>> ZyRHMQu1AQ&m=EoLwt0JuWdDOc1BU6xjU4le8GxWW0NB5xhp-20uHVws&s=C6m6fYEOP
> >>> l 79xkEzUw4GMTCpsV1JmEBJmKwXr5Gk4CQ&e=
> >>
> >>
> >>
> >> #####################################################################
> >> #
> >> ##
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> >> C
> >> RvvI7VX5j3HvibIuT3ZiarcKl5qtMPo&r=HK-CY_tL8CLLA93vdywyu3qI70R4H8oHzZy
> >> R
> >> HMQu1AQ&m=EoLwt0JuWdDOc1BU6xjU4le8GxWW0NB5xhp-20uHVws&s=C6m6fYEOPl79x
> >> k EzUw4GMTCpsV1JmEBJmKwXr5Gk4CQ&e= GSK monitors email communications
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