The Synthesis of Ethyl Acetamidocyanoacetate, DL-Lysine, DL-Ornithine and DL-Tyrosine Labeled with Isotopic Carbon<sup>1</sup>

Fields, Melvin; Walz, Doris E.; Rothchild, Seymour

doi:10.1021/ja01147a034

Cited by 36 publications

(4 citation statements)

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“…l-[methyI-2H3] Methionine (98 atom % 2H) was purchased from Merck Isotopes; proline (97 atom % 2H) and 3,4,4,5,proline (97 atom % 2H) were synthesized by the procedure of Young and Torchia (1983). dl-[6-15N] Lysine (95 atom % 15N) was synthesized by the general procedure of Fields et al (1951), starting with 15N-enriched 4-(bromobutyl) phthalimide, which was synthesized by the method of Drake and Carman (1949). DL-(4-Fluorophenyl)alanine was purchased from Aldrich or Calbiochem.…”

Section: Methodsmentioning

confidence: 99%

Molecular dynamics of collagen side chains in hard and soft tissues. A multinuclear magnetic resonance study

Sarkar

Hiyama²,

Niu³

et al. 1987

Biochemistry

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We have prepared samples of (a) intact calvaria collagen (cross-linked and mineralized), (b) intact tendon collagen (cross-linked but not mineralized), and (c) reconstituted chick calvaria collagen (not cross-linked and not mineralized) containing [methyl-2H3]methionyl, [4,4-2H2]pyrrolidinyl, (4-fluorophenyl)alanyl, and [6-15N]lysyl residues. Using multinuclear magnetic resonance spectroscopy, we have investigated the molecular dynamics of the labeled amino acids. Guided by model compound studies, we reached the following conclusions regarding collagen side chain dynamics from our analysis of line shapes and relaxation rates. At 22 degrees C, imino residues in all samples have flexible rings with root mean square angular fluctuations in the 11-30 degree range. Nearly all labeled amino acid side chains reorient about at least two side chain single bonds. At temperatures below -30 degrees C, most of these side chain motions are absent in all the samples. Surprisingly, in contrast with results obtained for backbone motions, side chain motions are only marginally more hindered in mineralized samples as compared with nonmineralized samples, a result we discuss with reference to collagen-mineral interactions. We also discuss the possible relationship between collagen dynamics and function.

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Section: Methodsmentioning

confidence: 99%

Molecular dynamics of collagen side chains in hard and soft tissues. A multinuclear magnetic resonance study

Sarkar

Hiyama²,

Niu³

et al. 1987

Biochemistry

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“…The combined filtrate and washings were concentrated to dryness in oacuo, 1. DL-(2-2H)Ornirhine (18) and the residue was repeatedly dissolved in water and evaporDierhyl2-ace~amido-2-(3-phrholimidopropyl)malona~e (3) ated to dryness to remove exchangeable deuterium. T h e (23) residue, crude ornithine dihydrochloride, was dissolved in hot Diethyl acetamidomalonate (2) (Aldrich Chemical Co.) (2.16 95% ethanol (8 mL), the solution was cooled to room temperag) was dissolved in hot dry ethanol4 in a two-necked round ture, filtered, and pyridine (ca.…”

Section: Fig 4 Ord Curves Of (-)-Methyl 4-phthalimido(4-*h)-butyratmentioning

confidence: 99%

The stereochemistry of the enzymic decarboxylation of L-arginine and of L-ornithine

Richards¹,

Spenser²

1982

Can. J. Chem.

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“…The ethyl cyanoacetate-2-C14 thus obtained was a yellow oil. I t was used to synthesize dl-tyrosine-2-C1%y the method of Fields et al (3). The yield of dl-tyrosine was 1.820 gin.…”

Section: Methodsmentioning

confidence: 99%

The Biogenesis of Alkaloids: Vii. The Formation of Hordenine and N-Methyltyramine From Tyrosine in Barley

Leete¹,

Marion²

1953

Can. J. Chem.

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The Synthesis of Ethyl Acetamidocyanoacetate, DL-Lysine, DL-Ornithine and DL-Tyrosine Labeled with Isotopic Carbon¹

Cited by 36 publications

References 1 publication

Molecular dynamics of collagen side chains in hard and soft tissues. A multinuclear magnetic resonance study

Molecular dynamics of collagen side chains in hard and soft tissues. A multinuclear magnetic resonance study

The stereochemistry of the enzymic decarboxylation of L-arginine and of L-ornithine

The Biogenesis of Alkaloids: Vii. The Formation of Hordenine and N-Methyltyramine From Tyrosine in Barley

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The Synthesis of Ethyl Acetamidocyanoacetate, DL-Lysine, DL-Ornithine and DL-Tyrosine Labeled with Isotopic Carbon1

Cited by 36 publications

References 1 publication

Molecular dynamics of collagen side chains in hard and soft tissues. A multinuclear magnetic resonance study

Molecular dynamics of collagen side chains in hard and soft tissues. A multinuclear magnetic resonance study

The stereochemistry of the enzymic decarboxylation of L-arginine and of L-ornithine

The Biogenesis of Alkaloids: Vii. The Formation of Hordenine and N-Methyltyramine From Tyrosine in Barley

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The Synthesis of Ethyl Acetamidocyanoacetate, DL-Lysine, DL-Ornithine and DL-Tyrosine Labeled with Isotopic Carbon¹