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Vasopressin pp 335–368Cite as

Selective Agonists and Antagonists of Vasopressin

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Abstract

Since the original synthesis of (arginine-) vasopressin (AVP) in 1954 (du Vig-neaud et al, 1954b), hundreds of analogues of VP and of oxytocin (OX) have been synthesized; their properties have been reported in numerous publications (see e.g., Berde and Boissonnas, 1968; Sawyer and Manning, 1973; Sawyer et al., 1981a; Manning et al., 1981a). Space considerations do not permit the inclusion of all the published analogues of VP and OX. Since the focus of this volume is on vasopressin, this chapter deals primarily with analogues—agonists and antagonists—of VP.

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Abbreviations

AVP:

(arginine-) vasopressin

hydroxy-AVP:

1-l-α-hydroxy-β-mercaptopropionic acid) arginine vasopressin

Abu:

α-aminobutyric acid

Asu:

α-aminosuberic acid

Aze:

azetidine-2-carboxylic acid

Cha:

cyclohexylalanine

Cit:

citrulline

Dab:

α-γ-diaminobutyric acid

Dap:

α-β-diaminopropionic acid

Dapt(Gly):

α-amino-β-(glycylamino)-propionic acid

DapG:

α-amino-β-guanidinopropionic acid

Har:

homoarginine

Hls:

homolysine

MeAla:

N-methylalanine

Nar:

norarginine

Nle:

norleucine

Nva:

norvaline

Orn:

ornithine

pGlu:

pyroglutamic acid

Δ3-Pro:

3,4-dehydroproline

Sar:

sarcosine

Tyr(Me):

O-methyltyrosine

Tyr(Et):

O-ethyltyrosine

Tyr(nPr):

O-n-propyltyrosine

Tyr(iPr):

O-isopropyltyrosine

AcP:

1-N-acetylpenicillamine

P:

1-penicillamine

Pen6 :

6-penicillamine

dP:

1-deaminopenicillamine or 1-(β-mercapto-β,β-dimethylpropionic acid)

dEt2 :

1-(β-mercapto-β,β-diethylpropionic acid)

d(CH2)5 :

1-(β-mercapto-β,β-I3-cyclopentamethylenepropionic acid).

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Authors and Affiliations

  1. Department of Biochemistry, Medical College of Ohio, Toledo, Ohio, 43699, USA

    Maurice Manning & Krzysztof Bankowski

  2. Department of Organic Chemistry, University of Warsaw, Warsaw, Poland

    Krzysztof Bankowski

  3. Department of Pharmacology, College of Physicians and Surgeons of Columbia University, New York, New York, 10032, USA

    Wilbur H. Sawyer

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  1. Maurice Manning
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  2. Krzysztof Bankowski
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  1. University of Rochester Medical Center, Rochester, New York, USA

    Don Marshall Gash

  2. Netherlands Institute for Brain Research, Amsterdam, The Netherlands

    Gerard J. Boer

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Manning, M., Bankowski, K., Sawyer, W.H. (1987). Selective Agonists and Antagonists of Vasopressin. In: Gash, D.M., Boer, G.J. (eds) Vasopressin. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-8129-1_8

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