Formation of carbamates of taurine and other amino acids during neutralization of tissue extracts with potassium carbonate/ bicarbonate

Sherry, A. Dean; Malloy, Craig R.; Jeffrey, F. M H; Chavez, Flavio; Srere, Hilary K.

doi:10.1016/0022-2364(90)90247-7

Cited by 15 publications

(7 citation statements)

References 13 publications

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“…Such adducts are unusual but not unprecedented; a similar N-terminal carbamate adduct is present in bacterial thymidylate synthase [52]. Such adducts form due to the nonenzymatic reaction of CO 2 with amines [53–55] and although ubiquitous, only become significant in structures for which adduct formation significantly enhances stability. Nevertheless, carbamate adducts play critical roles in many protein systems, including CO 2 transport by hemoglobin [56] and CO 2 fixation by RUBISCO [57].…”

Section: Iv: the N-terminal Disulfide Switchmentioning

confidence: 99%

The structural basis of XRCC1-mediated DNA repair

London

2015

DNA Repair

128

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Scaffold proteins play a central role in DNA repair by recruiting and organizing sets of enzymes required to perform multi-step repair processes. X-ray cross complementing group 1 protein (XRCC1) forms enzyme complexes optimized for single-strand break repair, but participates in other repair pathways as well. Available structural data for XRCC1 interactions is summarized and evaluated in terms of its proposed roles in DNA repair. Mutational approaches related to the abrogation of specific XRCC1 interactions are also discussed. Although substantial progress has been made in elucidating the structural basis for XRCC1 function, the molecular mechanisms of XRCC1 recruitment related to several proposed roles of the XRCC1 DNA repair complex remain undetermined.

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Section: Iv: the N-terminal Disulfide Switchmentioning

confidence: 99%

The structural basis of XRCC1-mediated DNA repair

London

2015

DNA Repair

128

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“…Since proline is an imino acid, this adduct is more properly referred to as a carbimate, and is to the best of our knowledge, the first example of a carbimate adduct identified in a biological system. The in vitro CO 2 adducts of various amino acids including proline have previously been studied by NMR (Dettman et al, 1985; Morrow et al, 1974; Myers and Nelson, 1990; Sherry et al, 1990). …”

Section: Resultsmentioning

confidence: 99%

Characterization of the Redox Transition of the XRCC1 N-terminal Domain

et al. 2014

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SUMMARY XRCC1, a scaffold protein involved in DNA repair, contains an N-terminal domain (X1NTD) that interacts specifically with DNA polymerase β. It was recently discovered that X1NTD contains a disulfide switch that allows it to adopt either of two metamorphic structures. In the present study we demonstrate that formation of an N-terminal proline carbimate adduct resulting from the non-enzymatic reaction of Pro2 with CO2 is essential for stabilizing the oxidized structure, X1NTDox. The kinetic response of X1NTDred to H2O2, monitored by NMR was determined to be very slow, consistent with involvement of the buried, kinetically trapped Cys12 residue, but was significantly accelerated by addition of protein disulfide isomerase or by Cu2+. NMR analysis of a sample containing the pol β polymerase domain, and both the reduced and oxidized forms of X1NTD indicates that the oxidized form binds to the enzyme 25-fold more tightly than the reduced form.

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“…(a) The seminal plasma, after treatment with PCA, was neutralized with KOH instead of K 2 CO 3 . This preventive measure was according to Sherry et al 19 who had observed that taurine, a possible candidate for the X compound, was derivatized to its carbamate in extract solutions during neutralization with bicarbonate. (b) The lyophilizates were titrated to pH 7.…”

Section: Resultsmentioning

confidence: 99%

“…19 The carbon assignments followed from the subsequent C,H chemical shift correlation. The large one-bond C,H coupling of 145 Hz (Table 1) confirmed the assignment of the N-CH 2 carbon (compare 145 Hz for CH 3 + NH 3 and 138 Hz for CH 3 SR).…”

Section: Hypotaurinementioning

confidence: 99%