Abstract
The stereochemistry of carotenoids can be conveniently discussed under three main headings: (i) geometrical isomerism about the carbon-carbon double bonds, (ii) conformation about the carbon-carbon single bonds, and (iii) the absolute configuration of any chiral groups.
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References
J. Herzig and F. Faltis, Ann. Chem. 431, 40 (1923).
P. Karrer, A. Helfenstein, R. Widmer and T. B. van Itallie, Helv. Chim. Acta 12, 741 (1929).
R. Kuhn and A. Winterstein, Ber. Deut. Chem. Ges. 66, 209 (1933).
A.E. Gillam and M.S. El Ridi, Nature 136, 914 (1935); Biochem. J. 30, 1735 (1936).
A.E. Gillam, M.S. El Ridi and S.K. Kon, Biochem. J. 31, 1605 (1937).
L. Zechmeister, Cis-trans Isomeric Carotenoids, Vitamins A and Arylpolyenes (Springer, Vienna 1962).
IUPAC-IUB Tentative Rules for the Nomenclature of Carotenoids, see Appendix of this book.
W. J. Rabourn, F.W. Quackenbush and J. W. Porter, Arch. Biochem. Biophys. 48, 267 (1954).
W.J. Rabourn and F.W. Quackenbush, Arch. Biochem. Biophys. 61, 111 (1956).
J.B. Davis, L.M. Jackman, P.T. Siddons and B.C.L. Weedon, J. Chem. Soc. C 1966, 2154.
O.B. Weeks, A.G. Andrewes, B.O. Brown and B.C.L. Weedon, Nature 224, 879 (1969); and unpublished results.
F.B. Jungalwala and J. W. Porter, Arch. Biochem. Biophys. 110, 291 (1965).
B.K. Koe and L. Zechmeister, Arch. Biochem. Biophys. 46, 100 (1953).
H. Claes, Z. Naturforsch. B 16, 445 (1961).
E. F. Magoon and L. Zechmeister, Arch. Biochem. Biophys. 68, 263 (1957).
A.L. Le Rosen and L. Zechmeister, J. Amer. Chem. Soc. 64, 1075 (1942).
L. Zechmeister and J.H. Pinckard, J. Amer. Chem. Soc. 69, 1930 (1947).
H. Claes, Z. Naturforsch. B 12, 401 (1957).
W. Rau and C. Zehender, Arch. Mikrobiol. 32, 423 (1959).
L. Zechmeister and W. A. Schroeder, J. Amer. Chem. Soc. 64, 1173 (1942).
N. Suzuki and K. Tsukida, Chem. Pharm. Bull. 7, 133 (1959).
B.O. Brown and B.C.L. Weedon, Chem. Commun. 1968, 382.
P. Karrer, C.H. Eugster and M. Faust, Helv. Chim. Acta 33, 300 (1950).
H.H. Strain, Arch. Biochem. Biophys. 48, 458 (1954).
J. Szabolcs and Gy. Tóth, Acta Chim. Acad. Sci. Hung. 63, 229 (1970).
H.H. Strain, W.M. Manning and G. Hardin, Biol. Bull. 86, 169 (1944).
A.L. Curl and G.F. Bailey, Food Res. 22, 323 (1957).
H. Nitsche and K. Egger, Phytochem. 8, 1577 (1969).
L. Cholnoky, K. Györgyfy, A. Rónai, J. Szabolcs, Gy. Tóth, G. Galasko, A.K. Mallams, E. S. Waight and B. C. L. Weedon, J. Chem. Soc. C 1969, 1256.
A. J. Aasen and S. Liaaen-Jensen, Acta Chem. Scand. 21, 2185 (1967).
S. Liaaen-Jensen, Pure Appl. Chem. 20, 421 (1969).
G. Wald, Angew. Chem. 80, 857 (1968).
O. Isler, Experientia 26, 225 (1970).
T. Reschke, Tetrahedron Letters 1969, 3435.
J.D. Bu’Lock, D.J. Austin, G. Snatzke and L. Hruban, Chem. Commun. 1970, 255.
P. F. Wareing and G. Ryback, Endeavour 29, 84 (1970).
S. Liaaen-Jensen, Kgl. Norske Videnskab. Selskabs Skrifter 1962, No. 8.
L. Zechmeister and R.B. Escue, J. Amer. Chem. Soc. 66, 322 (1944).
L. Zechmeister, A. L. LeRosen, W. A. Schroeder, A. Polgár and L. Pauling, J. Amer. Chem. Soc. 65, 1940 (1943).
B.C.L. Weedon, Rev. Pure Appl. Chem. (Australia) 20, 51 (1970).
L. Pauling, Fortschr. Chem. Org. Naturst. 3, 203 (1939).
N. Arpin and S. Liaaen-Jensen, Phytochem. 8, 185 (1969).
K. Schön, Biochem. J. 32, 1566 (1938).
B.C.L. Weedon, Fortschr. Chem. Org. Naturst. 27, 81 (1969).
H. H. Jaffé and M. Orchin, Theory and Applications of Ultraviolet Spectroscopy (Wiley, New York 1962).
K. Lunde and L. Zechmeister, J. Amer. Chem. Soc. 77, 1647 (1955).
M.S. Barber, J.B. Davis, L.M. Jackman and B.C.L. Weedon, J. Chem. Soc. 1960, 2870.
R.B. Bates and D.M. Gale, J. Amer. Chem. Soc. 82, 5749 (1960).
N. Nicolaides and F. Laves, J. Amer. Chem. Soc. 76, 2596 (1954).
C. v. Planta, U. Schwieter, L.H. Chopard-dit-Jean, R. Rüegg, M. Kofler and O. Isler, Helv. Chim. Acta 45, 548 (1962).
P.K. Korver, C. Kruk, P. J. van der Haak, J.L. Bass and H.O. Huisman, Tetrahedron 22, 277 (1966).
R.B. Bates, D.M. Gale and B.J. Grüner, J. Org. Chem. 28, 1086 (1963).
J. W.K. Burrell, R.F. Garwood, L.M. Jackman, E. Oskay and B.C.L. Weedon, J. Chem. Soc. C 1966, 2144.
G. Pattenden and B.C.L. Weedon, J. Chem. Soc. C 1968, 1984.
B.O. Brown, T. W. Goodwin and B.C.L. Weedon, unpublished results.
K. Tsukida, M. Yokota, H. Shimamoto and S. Cho, Vitamins (Japan) 38, 388 (1968).
K. Tsukida and M. Yokota, Vitamins (Japan) 38, 396 (1968).
U. Schwieter and S. Liaaen-Jensen, Acta Chem. Scand. 23, 1057 (1969).
P. Karrer and U. Solmssen, Helv. Chim. Acta 20, 1396 (1937).
L. Zechmeister and R.B. Escue, J. Amer. Chem. Soc. 66, 322 (1944).
P. Karrer and E. Jucker, Carotinoide (Birkhäuser, Basle 1948); English translation by E.A. Braude (Elsevier, Amsterdam 1950).
M.S. Barber, A. Hardisson, L.M. Jackman and B.C.L. Weedon, J. Chem. Soc. 1961, 1625.
L.M. Jackman and R.H. Wiley, J. Chem. Soc. 1960, 2881, 2886.
D. J. Patel, Nature 221, 825 (1969).
U. Schwieter, G. Englert, N. Rigassi and W. Vetter, Pure Appl. Chem. 20, 365 (1969).
T. W. Goodwin and R.J.H. Williams, Proc. Roy. Soc, Ser. B 163, 515 (1965).
T. W. Goodwin, Pure Appl. Chem. 20, 483 (1969).
O. Isler and P. Schudel, Advan. Org. Chem. 4, 115 (1963).
Sir Ian Heilbron and B.C.L. Weedon, Bull. Soc. Chim. France 1958, 83.
B.C.L. Weedon, Pure Appl. Chem. 20, 531 (1969).
O. Isler, H. Lindlar, M. Montavon, R. Rüegg, G. Saucy and P. Zeller, Helv. Chim. Acta 39, 2041 (1956).
O. Isler, A. Ronco, W. Guex, N.C. Hindley, W. Huber, K. Dialer and M. Kofler, Helv. Chim. Acta 32, 489 (1949).
P. Mildner and B.C.L. Weedon, J. Chem. Soc. 1953, 3294.
H. H. Inhoffen, O. Isler, G. von der Bey, G. Raspé, P. Zeller and R. Ahrens, Ann. Chem. 580, 7 (1953).
P.S. Manchand, R. Rüegg, U. Schwieter, P.T. Siddons and B.C.L. Weedon, J. Chem. Soc. 1965, 2019.
R. Kuhn, H.H. Inhoffen, H.A. Staab and W. Otting, Chem. Ber. 86, 965 (1953).
O. Isler, H. Gutmann, H. Lindlar, M. Montavon, R. Rüegg, G. Ryser and P. Zeller, Helv. Chim. Acta 39, 463 (1956).
G. Pattenden, J.E. Way and B.C.L. Weedon, J. Chem. Soc. C 1970, 235.
E. A. Braude, E. R. H. Jones, H. P. Koch, R. W. Richardson, F. Sondheimer and J. B. Toogood, J. Chem. Soc. 1949, 1890.
M. Yamaguchi, Bull. Chem. Soc. Japan 31, 51, 739 (1958); 33, 1560 (1960).
S. Liaaen-Jensen, E. Hegge and L.M. Jackman, Acta Chem. Scand. 18, 1703 (1964).
R. Bonnett, A.A. Spark and B.C.L. Weedon, Acta Chem. Scand. 18, 1739 (1964).
R. D. G. Cooper, J. B. Davis and B. C. L. Weedon, J. Chem. Soc. 1963, 5637.
S. Hertzberg, S. Liaaen-Jensen, C.R. Enzell and G.W. Francis, Acta Chem. Scand. 23, 3290 (1969).
E.L. Eichhorn and C.H. MacGillavry, Acta Crystallogr. 12, 872 (1959).
B. Koch and C.H. MacGillavry, Acta Crystallogr. 16, A 48 (1963).
C.H. Stam and C.H. MacGillavry, Acta Crystallogr. 16, 62 (1963).
C. Sterling, Acta Crystallogr. 17, 1224 (1964).
J.C. J. Bart and C.H. MacGillavry, Acta Crystallogr., Sect. B 24, 1587 (1968).
W.G. Sly, Acta Crystallogr. 17, 511 (1964).
J.C. J. Bart and C.H. MacGillavry, Acta Crystallogr., Sect. B 24, 1569 (1968).
C. A. Coulson, J. Chem. Phys. 7, 1069 (1939).
H.H. Inhoffen, F. Bohlmann, K. Bartram, G. Rummert and H. Pommer, Ann. Chem. 570, 54 (1950).
B. Pullman, J. Langlet and H. Berthod, J. Theor. Biol. 23, 492 (1969).
L. Zechmeister, L. Cholnoky and A. Polgár, Ber. Deut. Chem. Ges. 72, 1678 (1939).
R. Kuhn and C. Grundmann, Ber. Deut. Chem. Ges. 67, 596 (1934).
L. Zechmeister and L. Cholnoky, Ann. Chem. 543, 248 (1940).
I.M. Heilbron and R.F. Phipers, Biochem. J. 29, 1369 (1935).
P. Karrer, A. Helfenstein, H. Wehrli, B. Pieper and R. Morf, Helv. Chim. Acta 14, 614 (1931).
L. Zechmeister and P. Tuzson, Ber. Deut. Chem. Ges. 62, 2226 (1929).
R. Kuhn, A. Winterstein and E. Lederer, Hoppe-Seyler’s Z. Physiol. Chem. 197, 141 (1931).
P. Karrer and O. Walker, Helv. Chim. Acta 16, 641 (1933).
R. Kuhn and E. Lederer, Ber. Deut. Chem. Ges. 64, 1349 (1931).
P. Karrer, E. Jucker and J. Rutschmann, Helv. Chim. Acta 28, 1156 (1945).
R. Kuhn and A. Deutsch, Ber. Deut. Chem. Ges. 66, 883 (1933).
H.H. Strain, J. Biol. Chem. 123, 425 (1938).
A.L. Le Rosen and L. Zechmeister, Arch. Biochem. 1, 17 (1943).
R. Kuhn, A. Winterstein and W. Kaufmann, Ber. Deut. Chem. Ges. 63, 1489 (1930).
O. Isler, H. Lindlar, M. Montavon, R. Rüegg, G. Saucy and P. Zeller, Helv. Chim. Acta 39, 2041 (1956).
O. Isler, H. Lindlar, M. Montavon, R. Rüegg, G. Saucy and P. Zeller, Helv. Chim. Acta 40, 456 (1957).
R. Bonnett, A.K. Mallams, A.A. Spark, J.L. Tee, B.C.L. Weedon and A. McCormick, J. Chem. Soc. C 1969, 429.
P. Karrer, R. Morf, E. v. Krauss and A. Zubrys, Helv. Chim. Acta 15, 490 (1932).
N.J. Antia, Can. J. Chem. 43, 302 (1965).
L. Bartlett, W. Klyne, W. P. Mose, P. M. Scopes, G. Galasko, A. K. Mallams, B.C.L. Weedon, J. Szabolcs and Gy.Tóth, J. Chem. Soc. C 1969, 2527.
D. Goodfellow, W. Klyne, G.P. Moss, P.M. Scopes and B.C.L. Weedon, unpublished results.
M. Buchwald and W.P. Jencks, Biochemistry 7, 834, 844 (1968).
S. Liaaen-Jensen, private communication.
M.S. Barber, L.M. Jackman, C.K. Warren and B.C.L. Weedon, Proc. Chem. Soc. 1960, 19; J. Chem. Soc. 1961, 4019.
R. Entschel and P. Karrer, Helv. Chim. Acta 43, 89 (1960).
H. Faigle and P. Karrer, Helv. Chim. Acta 44, 1257 (1961).
H. Faigle and P. Karrer, Helv. Chim. Acta 44, 1904 (1961).
L. Cholnoky and J. Szabolcs, Experientia 16, 483 (1960).
K. Freudenberg and W. Lwowski, Ann. Chem. 587, 213 (1954); 594, 76 (1955).
R.D.G. Cooper, L.M. Jackman and B.C.L. Weedon, Proc. Chem. Soc. 1962, 215.
J. W. Faigle, H. Müller, W. von Philipsborn and P. Karrer, Helv. Chim. Acta 47, 741 (1964).
R. Bowden and B.C.L. Weedon, unpublished results.
B.C.L. Weedon, Chem. in Britain 3, 424 (1967).
J. Bredt, Ann. Chem. 395, 26 (1913).
A. Marquet, M. Dvolaitzky and D. Arigoni, Bull. Soc. Chim. France 1966, 2956. Carotenoids 21
F.H. Allen and D. Rogers, Chem. Commun. 1966, 837.
A. Jensen, Acta Chem. Scand. 15, 1605 (1961).
L. Cholnoky, J. Szabolcs and Gy. Tóth, Ann. Chem. 708, 218 (1967).
J.S. Narozanski, S.W. Russell and B.C.L. Weedon, unpublished results.
P. Nayler and M.C. Whiting, J. Chem. Soc. 1954, 4006.
T. Miki and Y. Hara, Pharm. Bull. 4, 89 (1956).
S.W. Russell and B.C.L. Weedon, Chem. Commun. 1969, 85.
S.W. Russell and B.C.L. Weedon, unpublished results.
T.E. DeVille, M. B. Hursthouse, S.W. Russell and B. C. L. Weedon, Chem. Commun. 1969, 754.
T.E. DeVille, M. B. Hursthouse, S.W. Russell and B. C. L. Weedon, Chem. Commun. 1969, 1311.
J.M. Bijvoet, Endeavour 14, 71 (1955).
G. Galasko, J. Hora, T.P. Toube, B. C. L. Weedon, D. André, M. Barbier, E. Lederer and V.R. Villanueva, J. Chem. Soc. C 1969, 1264.
J. Hora, T.P. Toube and B.C.L. Weedon, J. Chem. Soc. C 1970, 241.
H.F. Taylor and R.S. Burden, Phytochem. 9, 2217 (1970).
P. Karrer, Fortschr. Chem. Org. Naturst. 5, 1 (1948).
P. Karrer and E. Jucker, Helv. Chim. Acta 28, 300 (1945).
J. Meinwald, K. Erickson, M. Hartshorn, Y.C. Meinwald and T. Eisner, Tetrahedron Letters 1968, 2959.
J. Meinwald and L. Hendry, Tetrahedron Letters 1969, 1657.
S. Isoe, S.B. Hyeon, H. Ichikawa, S. Katsumura and T. Sakan, Tetrahedron Letters 1968, 5561.
M. Mousseron-Canet, J.-P. Dalle and J.-C. Mani, Tetrahedron Letters 1968, 6037.
C.S. Foote and M. Brenner, Tetrahedron Letters 1968, 6041.
D.E. Loeber, S.W. Russell, T.RToube and B.C.L. Weedon, J. Chem. Soc. C 1971, 404.
T.E. DeVille, J. Hora, M.B. Hursthouse, T.RToube and B.C.L. Weedon, Chem. Commun. 1970, 1231.
W. Fenical, D.R. Kearns and P. Radlick, J. Amer. Chem. Soc. 91, 3396 (1969).
D.R. Kearns, J. Amer. Chem. Soc. 91, 6554 (1969).
K. Tsukida, S. Cho and M. Yokota, Chem. Pharm. Bull. 17, 1755 (1969)
L. Hendry, private communication.
J.W Cornforth, W. Draber, B.V. Milborrow and G. Ryback, Chem. Commun. 1967, 114.
J.W. Cornforth, B.V. Milborrow and G. Ryback, Nature 206, 715 (1965).
J. A. Mills, J. Chem. Soc. 1952, 4976.
P.F. Wareing and G. Ryback, Endeavour 29, 84 (1970).
H.F. Taylor and T.A. Smith, Nature 215, 1513 (1967).
H.F. Taylor, Soc. Chem. Ind. London Monograph 1968, No. 31, 22.
T. Wada, Chem. Pharm. Bull. 13, 43 (1965).
G. Snatzke, H. Schwang and P. Welzel, Some New Methods in Structural Chemistry (United Trade Press, London 1967).
A.J. Davies and B.C.L. Weedon, unpublished results.
H. Sobotka, E. Bloch, H. Cahnmann, E. Feldbau and E. Rosen, J. Amer. Chem. Soc. 65, 2061 (1943).
C. Tscharner, C. H. Eugster and P. Karrer, Helv. Chim. Acta 40, 1676 (1957); 41, 32 (1958).
C.H. Eugster, R. Buchecker, C. Tscharner, G. Uhde and G. Ohloff, Helv. Chim. Acta 52, 1729 (1969).
R. Buchecker, H. Yokoyama and C. H. Eugster, Helv. Chim. Acta 53, 1210 (1970).
Y.R. Naves and G.R. Parry, Helv. Chim. Acta 30, 419 (1947).
Y.R. Naves, Helv. Chim. Acta 32, 1064 (1949).
D. La Face, Helv. Chim. Acta 33, 249 (1950).
Y. R. Naves, Perfum. Essent. Oil Rec. 55, 658 (1964).
M. Winter and E. Sundt, Helv. Chim. Acta 45, 2195 (1962).
M. Soucek and P. Vlad, Collect. Czech. Chem. Commun. 28, 1211 (1963).
B.C.L. Weedon, in Chemistry and Biochemistry of Plant Pigments, ed. by T.W. Goodwin (Academic Press, London 1965), p. 86.
H. Müller and P. Karrer, Helv. Chim. Acta 48, 291 (1965).
T.J. Walton, G. Britton and T.W. Goodwin, Biochem. J. 112, 383 (1969).
D. Goodfellow, G.P. Moss and B.C.L. Weedon, Chem. Commun. 1970, 1578.
E. Nicoară, G. Illyes, M. Şuteu and C. Bodea, Rev. Roumaine Chim. 12, 547 (1967).
D.J. Austin, J.D. Bu’Lock and D. Drake, Experientia 26, 348 (1970).
W. V. E. Doering and R. W. Young, J. Amer. Chem. Soc. 74, 2997 (1952).
G. Snatzke and K. Schaffner, Helv. Chim. Acta 51, 986 (1968).
R.S. Cahn and C.K. Ingold, J. Chem. Soc. 1951, 612.
R.S. Cahn, C.K. Ingold and V. Prelog, Experientia 12, 81 (1956).
R.S. Cahn, Sir Christopher Ingold and V. Prelog, Angew. Chem., Int. Ed. Engl. 5, 385 (1966).
R.S. Cahn, J. Chem. Educ. 41, 116 (1964).
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Weedon, B.C.L. (1971). Stereochemistry. In: Isler, O., Gutmann, H., Solms, U. (eds) Carotenoids. Chemische Reihe, vol 23. Birkhäuser, Basel. https://doi.org/10.1007/978-3-0348-5831-1_5
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