The Synthesis of an Octapeptide Amide With the Hormonal Activity of Oxytocin

Vigneaud, Vincent du; Ressler, Charlotte; Swan, College John M.; Roberts, Carleton W.; Katsoyannis, Panayotis G.; Gordon, Samuel

doi:10.1021/ja01115a553

Cited by 539 publications

(170 citation statements)

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“…18,19 As structure determinations of peptides in the 1950s precluded the use of modern instrumentation (HPLC, mass spectrometry, high resolution NMR), careful degradative studies, coupled with accurate amino acid analyses, led to a proposed structure for oxytocin which featured a nonapeptide amide containing a disulfide bridge. 22 The synthesis of such a structure in 1953 was formidable task and it was far from obvious how to synthesize a molecule with a disulfide bridge that forms a 20-atom ring containing six of the nine residues present in the molecule. Wieland and Bodanszky have discussed the details of the first and subsequent syntheses of oxytocin.…”

Section: Emil Fischer (1852-1919)mentioning

confidence: 99%

Bruce Merrifield and solid‐phase peptide synthesis: A historical assessment

Mitchell

2008

Biopolymers

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Bruce Merrifield, trained as a biochemist, had to address three major challenges related to the development and acceptance of solid‐phase peptide synthesis (SPPS). The challenges were (1) to reduce the concept of peptide synthesis on a insoluble support to practice, (2) overcome the resistance of synthetic chemists to this novel approach, and (3) establish that a biochemist had the scientific credentials to effect the proposed revolutionary change in chemical synthesis. How these challenges were met is discussed in this article. © 2008 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 90: 175–184, 2008.This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com

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Section: Emil Fischer (1852-1919)mentioning

confidence: 99%

Bruce Merrifield and solid‐phase peptide synthesis: A historical assessment

Mitchell

2008

Biopolymers

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“…The protected peptide was treated with trifluoracetic acid for 20 min to remove the t-BOC group, and after isolation by the addition of ether, was exposed to sodium in liquid ammonia according to the method of du Vigneaud et al [ 15]. The remaining free thiol groups were oxidised by air at pH 6.8 [14].…”

Section: Synthesis Of 2 H-and L Sn-labelled Oxytocinsmentioning

confidence: 99%

Unequivocal assignments of NH proton magnetic resonance bands in oxytocin using ²H‐ and ¹⁵N‐substituted molecules

Bradbury¹,

Burgen²,

Feeney³

et al. 1974

FEBS Letters

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“…lactation ͉ maternal behavior ͉ ultrasonic vocalization ͉ social discrimination ͉ aggressive behavior O xytocin (OXT), a nonapeptide hormone, was the first peptide hormone whose structure was determined and the first to be chemically synthesized in a biologically active form (1,2). OXT is produced primarily in the paraventricular and supraoptic nuclei of the hypothalamus (3) and secreted mainly from the posterior pituitary gland.…”

mentioning

confidence: 99%

Pervasive social deficits, but normal parturition, in oxytocin receptor-deficient mice

Takayanagi

Yoshida

Bielsky

et al. 2005

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

697

596

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The oxytocin receptor (OXTR) and its ligand, oxytocin (OXT), regulate reproductive physiology (i.e., parturition and lactation) and sociosexual behaviors. To define the essential functions of OXTR, we generated mice with a null mutation in the Oxtr gene (Oxtr ؊/؊ ) and compared them with OXT-deficient (Oxt ؊/؊ ) mice. Oxtr ؊/؊ mice were viable and had no obvious deficits in fertility or reproductive behavior. Oxtr ؊/؊ dams exhibited normal parturition but demonstrated defects in lactation and maternal nurturing. Infant Oxtr ؊/؊ males emitted fewer ultrasonic vocalizations than wild-type littermates in response to social isolation. Adult Oxtr ؊/؊ males also showed deficits in social discrimination and elevated aggressive behavior. Ligand Oxt ؊/؊ males from Oxt ؊/؊ dams, but not from Oxt ؉/؊ dams, showed similar high levels of aggression. These data suggest a developmental role for the OXT͞OXTR system in shaping adult aggressive behavior. Our studies demonstrate that OXTR plays a critical role in regulating several aspects of social behavior and may have important implications for developmental psychiatric disorders characterized by deficits in social behavior.lactation ͉ maternal behavior ͉ ultrasonic vocalization ͉ social discrimination ͉ aggressive behavior

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The Synthesis of an Octapeptide Amide With the Hormonal Activity of Oxytocin

Cited by 539 publications

References 1 publication

Bruce Merrifield and solid‐phase peptide synthesis: A historical assessment

Bruce Merrifield and solid‐phase peptide synthesis: A historical assessment

Unequivocal assignments of NH proton magnetic resonance bands in oxytocin using ²H‐ and ¹⁵N‐substituted molecules

Pervasive social deficits, but normal parturition, in oxytocin receptor-deficient mice

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The Synthesis of an Octapeptide Amide With the Hormonal Activity of Oxytocin

Cited by 539 publications

References 1 publication

Bruce Merrifield and solid‐phase peptide synthesis: A historical assessment

Bruce Merrifield and solid‐phase peptide synthesis: A historical assessment

Unequivocal assignments of NH proton magnetic resonance bands in oxytocin using 2H‐ and 15N‐substituted molecules

Pervasive social deficits, but normal parturition, in oxytocin receptor-deficient mice

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Unequivocal assignments of NH proton magnetic resonance bands in oxytocin using ²H‐ and ¹⁵N‐substituted molecules