Synthesis of fragments of human β‐lipotropin, β<sub>h</sub>‐LPH. Part I. The synthesis of β‐LPH‐(61‐76) and β‐LPH‐(61‐77), i.e. α‐ and γ‐endorphin, respectively

Bijl, W. A. A. J.; Nispen, J. W. van; Greven, H. M.

doi:10.1002/recl.19790981205

Recl. Trav. Chim. Pays‐Bas

1979

DOI: 10.1002/recl.19790981205

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Synthesis of fragments of human β‐lipotropin, β_h‐LPH. Part I. The synthesis of β‐LPH‐(61‐76) and β‐LPH‐(61‐77), i.e. α‐ and γ‐endorphin, respectively

W. A. A. J. Bijl¹,

J. W. van Nispen²,

H. M. Greven³

Abstract: The synthesis of β‐LPH‐(61–76) and β‐LPH‐(61–77) [i.e. α‐ and γ‐endorphin, respectively] by means of the fragment condensation approach is described. Several of the fragments leading to these two endorphins were also obtained as pure, free peptides.

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Cited by 12 publications

References 25 publications

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FAB and tandem mass spectrometry for endorphin- and ACTH peptides of molecular weight to 2000

Tomer¹,

Gross²,

Zappey³

et al. 1988

Biol. Mass Spectrom.

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Four beta-endorphins (beta-endorphin 6-17, 2-17, 1-16, and 1-17) and two adrenocorticotropic hormone (ACTH) peptides (ACTH 1-10 and (1-16)-NH2) were studied by using fast atom bombardment coupled with tandem mass spectrometry. The capability to reproduce metastable ion and collisionally activated decomposition spectra on two different commercial sector mass spectrometers in two different laboratories was found to be acceptable (deviations in relative abundance are less than +/- 50%). The endorphin peptides fragment metastably or upon collisional activation to give abundant B-series ions as well as Y-series ions, whereas Y-series ions are the principal ionic species produced upon the desorption by fast atom bombardment. The ACTH peptides also fragment to give Y-series ions, but of relatively low abundance compared to those from the endorphins. For both sets of peptides, high-energy collisionally activated decomposition and metastable ion decomposition daughter ion spectra are precise, structurally informative--even for peptides up to m/z 2000--and complementary to spectra of daughter ions produced by desorption ionization alone.

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FAB and tandem mass spectrometry for endorphin- and ACTH peptides of molecular weight to 2000

Tomer¹,

Gross²,

Zappey³

et al. 1988

Biol. Mass Spectrom.

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: SYNTHESIS OF FRAGMENTS OF HUMAN β‐LIPOTROPIN, βH‐LPH. PART I. THE SYNTHESIS OF β‐LPH‐(61‐76) AND β‐LPH‐(61‐77), I.E. α‐ AND Γ‐ENDORPHIN, RESPECTIVELY

Bijl¹,

Nispen²,

Greven³

1980

Chemischer Informationsdienst

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Die Synthese der Titelverbindungen (VIIIa) (oz‐Endorphin) und (VIIIb) (y‐Endorphin) erfolgt nach klassischen Kondensationsmethoden mit Hilfe der Fragmente (IIIb) + (IVb) bzw. (VId) ‐ die ihrerseits ausgehend von den (wie üblich schrittweise aufgebauten) Fragmenten (I)+(II) [→(IIIa)‐(IIIb)] bzw. (IV) + (V) [→(VIa), (VIc)‐(VIb), (VId)] dargestellt werden ‐ und Schutzgruppenabspaltung aus den Produkten (VIIa) bzw. (VIIb) mit TFA.

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Synthesis of fragments of human β‐lipotropin, β_h‐LPH. Part IV*. The synthesis of shortened peptides related to des‐1‐tyrosine‐γ‐endorphin [β‐LPH‐(62‐77)]

Greven¹,

Nispen²,

Bijl³

1980

Recl. Trav. Chim. Pays‐Bas

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Synthesis of fragments of human P-lipotropin, P,-LPH be obtained (as calculated from eq. 1) which correlate with the experimental peroxidation rate constants for many aromatic molecules over a range of more than eight orders of magnitude. For reasons not yet fully understood, the most serious exceptions are 9, I0-dimethylanthracene and di benzan thracene. Given such limitations, we feel that the present data show that a simple FMO approach gives a satisfactory description of the reactivity of singlet oxygen towards many aromatic molecules. Furthermore, the applicability of the FMO model confirms that the endoperoxidation is adequately described by a [4x + 2x]-cycloaddition mechanism and that the progress of bond formation in the transition state shows little dependence on the reactivity of the aromatic substrate. It seems unlikely that the alternative stepwise pathway for the addition of singlet oxygen to diene-systems, proposed by Detour C.S. 19, can explain the correlation between reaction rates and FMO energies. Abstract. The synthesis of several peptides related to P-LPH-(62-77) but shortened from the Nterminal end, is described. In these syntheses use has been made of the classical fragment condensation approach.

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Synthesis of fragments of human β‐lipotropin, β_h‐LPH. Part I. The synthesis of β‐LPH‐(61‐76) and β‐LPH‐(61‐77), i.e. α‐ and γ‐endorphin, respectively

Abstract: The synthesis of β‐LPH‐(61–76) and β‐LPH‐(61–77) [i.e. α‐ and γ‐endorphin, respectively] by means of the fragment condensation approach is described. Several of the fragments leading to these two endorphins were also obtained as pure, free peptides.

Cited by 12 publications

References 25 publications

FAB and tandem mass spectrometry for endorphin- and ACTH peptides of molecular weight to 2000

FAB and tandem mass spectrometry for endorphin- and ACTH peptides of molecular weight to 2000

ChemInform Abstract: SYNTHESIS OF FRAGMENTS OF HUMAN β‐LIPOTROPIN, βH‐LPH. PART I. THE SYNTHESIS OF β‐LPH‐(61‐76) AND β‐LPH‐(61‐77), I.E. α‐ AND Γ‐ENDORPHIN, RESPECTIVELY

Synthesis of fragments of human β‐lipotropin, β_h‐LPH. Part IV*. The synthesis of shortened peptides related to des‐1‐tyrosine‐γ‐endorphin [β‐LPH‐(62‐77)]

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Synthesis of fragments of human β‐lipotropin, βh‐LPH. Part I. The synthesis of β‐LPH‐(61‐76) and β‐LPH‐(61‐77), i.e. α‐ and γ‐endorphin, respectively

Abstract: The synthesis of β‐LPH‐(61–76) and β‐LPH‐(61–77) [i.e. α‐ and γ‐endorphin, respectively] by means of the fragment condensation approach is described. Several of the fragments leading to these two endorphins were also obtained as pure, free peptides.

Cited by 12 publications

References 25 publications

FAB and tandem mass spectrometry for endorphin- and ACTH peptides of molecular weight to 2000

FAB and tandem mass spectrometry for endorphin- and ACTH peptides of molecular weight to 2000

ChemInform Abstract: SYNTHESIS OF FRAGMENTS OF HUMAN β‐LIPOTROPIN, βH‐LPH. PART I. THE SYNTHESIS OF β‐LPH‐(61‐76) AND β‐LPH‐(61‐77), I.E. α‐ AND Γ‐ENDORPHIN, RESPECTIVELY

Synthesis of fragments of human β‐lipotropin, βh‐LPH. Part IV*. The synthesis of shortened peptides related to des‐1‐tyrosine‐γ‐endorphin [β‐LPH‐(62‐77)]

Contact Info

Product

Resources

About

Synthesis of fragments of human β‐lipotropin, β_h‐LPH. Part I. The synthesis of β‐LPH‐(61‐76) and β‐LPH‐(61‐77), i.e. α‐ and γ‐endorphin, respectively

Synthesis of fragments of human β‐lipotropin, β_h‐LPH. Part IV*. The synthesis of shortened peptides related to des‐1‐tyrosine‐γ‐endorphin [β‐LPH‐(62‐77)]