Perdeuterated biuret hydrate C2D5N3O2.(0.77D2O)

Craven, B. M.

doi:10.1107/s0567740873004851

Cited by 11 publications

(12 citation statements)

References 3 publications

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“…A similar pattern of changes in lengths and, hence, in the electronic structures of the ureido C=O and C-N bonds of urea (13) and biuret (14) has been observed. Interestingly, in the case of monomethyl urea (15), where the nitrogen substituent is the tetrahedral and electron-releasing methyl group (as opposed to the trigonal and electron-withdrawing carbomethoxy or carbamide group), the depolarization of the C=O bond is less severe and neither C-N bond appears to be affected by the substitution.…”

supporting

confidence: 69%

Molecular structure and intermolecular interactions of N1'-methoxycarbonylbiotin methyl ester: a model for carboxybiotin.

Stallings¹,

Monti²,

Lane³

et al. 1980

Proc. Natl. Acad. Sci. U.S.A.

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The crystal structure of N1'-methoxycarbonylbiotin methyl ester, a model for M'-carboxybiotin, has been determined. The In the first half-reaction, enzyme-bound biotin is carboxylated at Ni', generating N1'-carboxybiotin (II). In the second halfreaction, C02 is transferred, as a carboxyl group, from carboxybiotin to another molecule. Biotin enzymes are, in general, high molecular weight, multisubunit structures; the half-reactions generally occur at separate active sites which are located on different subunits of the enzymes.Here, we report the molecular structure of N1'-methoxycarbonylbiotin methyl ester (III), which is a model for Ni'-carboxybiotin (II). Structural results were obtained by using the technique of single-crystal x-ray diffraction. Previous crystallographic studies have established the molecular structures of free biotin (I) (2), dethiobiotin (3), azabiotin (4), oxybiotin, selenobiotin, biotin methyl ester, biotin sulfone, and biotin-d-sulfoxide, and carbobiotin (5). Differences between the molecular geometries and therefore the electronic configurations of the ureido moieties of I and III are of great interest because the ureido ring is the catalytically active portion of the biotin molecule. The previous studies have stressed the notion that, in free biotin and its'derivatives, the polarized forms of the biotin resomers (those with 'formal charge separation)

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supporting

confidence: 69%

Molecular structure and intermolecular interactions of N1'-methoxycarbonylbiotin methyl ester: a model for carboxybiotin.

Stallings¹,

Monti²,

Lane³

et al. 1980

Proc. Natl. Acad. Sci. U.S.A.

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“…3), being constrained in this conformation by a relatively strong intramolecular hydrogen bond between N(12) (donor) and N(21) (acceptor). A similar situation can be noted in the analogous compounds biuret hydrate1" (III, R=-NHz) (Hughes, Yakel & Freeman, 1961;Craven, 1973) The superscripts refer to atoms generated by the application of the following symmetry operations to the positions listed in Table 1 (1) 6861 (3) 1223 (5) 4498 (2) 88 (3) 240 (10) 58 (3) 17 (5) 41 (2) 12 (4) C (2) 7881 (3) 4610 (5) 6126 (2) 92 (3) 214 (10) 53 (3) 15 (4) 36 (2) 18 (4) N(1 I) 5570 (3) -574 (5) 3676 (2) 134 (4) 300 (11) 80 (3) 38 (5) 68 (3) 39 (4) N (12) 8127 (3) 1533 (5) 4323 (3) 144 (4) 419 (13) 91 (3) --18 (6) 86 (3) -22 (5) N (21) 9381 (3) 4952 (5) 6350 (2) 104 ( C--N bond lengths reported for the protonated biguanide derivatives paludrin* (1.307 A < C-N < 1.345 /~ (Brown, 1967) and morpholine biguanide'~ (1.311/~ _< C-N < 1.376 ,/k) (Handa & Saha, 1973).…”

supporting

confidence: 67%

Biguanide

Ernst¹,

Cagle²

1977

Acta Crystallogr B Struct Sci

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“…Crystallographic studies of allantoin suggest that the ureido group projects perpendicular to the plane of the hydantoin ring in much the same way that the tail of a scorpion extends above its body (10). OXLU and its close relative, biuret, on the other hand, are relatively planar (6).…”

Section: And 8)mentioning

confidence: 99%

Allantoin transport in Saccharomyces cerevisiae is regulated by two induction systems

et al. 1987

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We show that the allantoin transport system of Saccharomyces cerevisiae responds to two induction systems, one mediated by allophanate or its analog oxalurate and the other mediated by allantoin or its analog hydantoin acetate. The effects of the two inducers were additive in strain M85. Like other allantoin pathway genes, oxalurate-mediated induction of allantoin transport required a functional DAL8I gene product. Hydantoin acetate-mediated induction of the system, on the other hand, occurred normally in dai8) mutants. This suggests that induction was not only mediated by two separate inducers, but also involved different regulatory proteins.

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Perdeuterated biuret hydrate C₂D₅N₃O₂.(0.77D₂O)

Cited by 11 publications

References 3 publications

Molecular structure and intermolecular interactions of N1'-methoxycarbonylbiotin methyl ester: a model for carboxybiotin.

Molecular structure and intermolecular interactions of N1'-methoxycarbonylbiotin methyl ester: a model for carboxybiotin.

Biguanide

Allantoin transport in Saccharomyces cerevisiae is regulated by two induction systems

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