Structural Formula Vector Image
Title: Clupeine
CAS Registry Number: 9007-31-2
Literature References: Protamine found in herring (Clupea pallasii) sperm. Isoln from herring testes contg ripe sperm: Kossel, The Protamines and Histones (London, 1928); Rasmussen, Z. Physiol. Chem. 224, 97 (1934); Felix, Mager, ibid. 249, 111 (1937); Block et al., Proc. Soc. Exp. Biol. Med. 70, 494 (1949). Separated into two main fractions, Y and Z, and fraction Y separated into YI and YII: Ando, Sawada, J. Biochem. (Tokyo) 49, 252 (1961). Chemical structure of fraction Z: Ando et al., Biochim. Biophys. Acta 56, 628 (1962); Felix, Hashimoto, Z. Physiol. Chem. 330, 205 (1963). Complete amino acid sequence of Z component: Iwai et al., J. Biochem. (Tokyo) 69, 493 (1971); of YII component: Suzuki, Ando, ibid. 72, 1419 (1972); of YI component: eidem, ibid. 1433. Solid-phase synthesis of clupeine Z: Yonezawa et al., C.A. 79, 19093k (1973).
Properties: White powder, strongly alkaline reaction. pKa 7.4-8.0; pKb 2.9-3.3.
pKa: pKa 7.4-8.0; pKb 2.9-3.3
Derivative Type: Disulfate
Properties: White powder, [a]D22 -85.49° (satd aq soln). One gram dissolves in 80 ml water at room temp. Freely sol in hot water, separates from the supersatd soln on cooling as a clear, colorless oil contg 50% H2O, nD20 1.4435. Clupeine is split by protaminase, active trypsin and by chymotrypsin. Compds of clupeine with nucleic acids are described by Kossel, loc. cit.
Optical Rotation: [a]D22 -85.49° (satd aq soln)
Index of refraction: nD20 1.4435

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