The synthesis and characterization of 2,3-methanopyroglutamic acid

Mapelli, Claudio; Elrod, Luther F.; Holt, Elizabeth M.; Stammer, Charles H.

doi:10.1016/s0040-4020(01)89074-8

Cited by 16 publications

(11 citation statements)

References 12 publications

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“…Nevertheless, if only the position of the β‐substituents is considered, rather than the type, then the analogous structures for ΔAbu and ΔVal residues can be analysed. It has been found that the ΔVal analogues adopt primarily conformations α and β29, 31, 32, 34–40, 42, 43, 45, 50, 53, 55, 58, 60. The conformation β2 can also be found36, 40.…”

Section: Resultsmentioning

confidence: 99%

The conformational properties of α,β‐dehydroamino acids with a C‐terminal ester group

Siodłak

Broda

2011

Journal of Peptide Science

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α,β-Dehydroamino acid esters occur in nature. To investigate their conformational properties, a systematic theoretical analysis was performed on the model molecules Ac-ΔXaa-OMe [ΔXaa = ΔAla, (E)-ΔAbu, (Z)-ΔAbu, ΔVal] at the B3LYP/6-311+ + G(d,p) level in the gas phase as well as in chloroform and water solutions with the self-consistent reaction field-polarisable continuum model method. The Fourier transform IR spectra in CCl(4) and CHCl(3) have been analysed as well as the analogous solid state conformations drawn from The Cambridge Structural Database. The ΔAla residue has a considerable tendency to adopt planar conformations C5 (ϕ, ψ ≈ - 180°, 180°) and β2 (ϕ, ψ ≈ - 180°, 0°), regardless of the environment. The ΔVal residue prefers the conformation β2 (ϕ, ψ ≈ - 120°, 0°) in a low polar environment, but the conformations α (ϕ, ψ ≈ - 55°, 35°) and β (ϕ, ψ ≈ - 55°, 145°) when the polarity increases. The ΔAbu residues reveal intermediate properties, but their conformational dispositions depend on configuration of the side chain of residue: (E)-ΔAbu is similar to ΔAla, whereas (Z)-ΔAbu to ΔVal. Results indicate that the low-energy conformation β2 is the characteristic feature of dehydroamino acid esters. The studied molecules constitute conformational patterns for dehydroamino acid esters with various side chain substituents in either or both Z and E positions.

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Section: Resultsmentioning

confidence: 99%

The conformational properties of α,β‐dehydroamino acids with a C‐terminal ester group

Siodłak

Broda

2011

Journal of Peptide Science

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“…The aminolactone 11, which was isolated in 41 % yield, had previously been obtained as a side product in small quantities. [20] Another favorable use of the α,β-dehydroamino acid ester 2 would be in the synthesis of octahydro[2H]pyrazino-[1,2-a]pyrazine derivatives of type 16, a class of geometrically constrained peptidomimetics. [21] The approach to such compounds from 2 would start with the transformation to 3-spirocyclopropanated 5-oxopiperazine-2-carboxylates of type 15, some of which were synthesized [21] from 1-Me in four steps in overall yields of ca.…”

Section: Resultsmentioning

confidence: 99%

Methyl 2‐(Benzyloxycarbonylamino)‐2‐cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl‐Containing Amino Acids

et al. 2009

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Keywords: Cyclopropanes / Amino acids / Michael addition / Peptidomimetics / Molecular diversity Methyl 2-(benzyloxycarbonylamino)-2-cyclopropylideneacetate (2) was prepared in nine steps starting from L-serine in an overall yield of 24 %. It has been demonstrated to be reasonably reactive in Michael additions of various nucleophiles (6 examples, 75-98 % yields) as well as Diels-Alder reactions, both leading to new cyclopropyl-containing amino acids in protected form. An application of 2 in the synthesis of methyl

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“…Under identical conditions, reaction of dihydrooxazolone 65a with ethoxycarbonyl methylidenedimethylsulfurane (60b) gives a mixture of diastereomers (3 : 1) ( 1 H and 13 C NMR spectroscopic data) in a total yield of 97%. 63…”

Section: Addition Of Stabilised Sulfur Ylides To Dipolarophilesmentioning

confidence: 99%

“…12 Studies of reactions of enzymes with peptide analogues of substrates containing cyclopropane derivatives of amino acids have shown that these fragments increase the hydrolytic stability of peptides. 13,14 Among other derivatives of compound 1, a special place is occupied by 1-aminocyclopropane-1,2-dicarboxylic (2,3-methanoaspartic, cycloaspartic, HAsp) { acid (2), a conformationally rigid analogue of aspartic acid. Its Z and E isomers are monoconformational analogues of `condensed' and `extended' conformations of glutamic acid (3), as regards the distance between the amino and 5-carboxy groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of 1-aminocyclopropane-1,2-dicarboxylic acid and compounds incorporating it

Краснов¹,

Korolyova²,

Левит³

2003

Russ. Chem. Rev.

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The synthesis and characterization of 2,3-methanopyroglutamic acid

Cited by 16 publications

References 12 publications

The conformational properties of α,β‐dehydroamino acids with a C‐terminal ester group

The conformational properties of α,β‐dehydroamino acids with a C‐terminal ester group

Methyl 2‐(Benzyloxycarbonylamino)‐2‐cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl‐Containing Amino Acids

Synthesis and properties of 1-aminocyclopropane-1,2-dicarboxylic acid and compounds incorporating it

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