Book Review: Biochemie (Biochemistry). By A. L. Lehninger. Translated by K. Fischer and R. Ries

Jaenicke, L.

doi:10.1002/anie.197603182

Cited by 2 publications

(6 citation statements)

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“…The standard Wittig reagents provide better yields throughout, but inferior stereoselectivities. The preparation of (3Z,5E)-1,3,5-undecatriene [49,50] (4 a, aldehyde R'' H 9 C 4 ), a stereoisomer of galbanum constituents [49] and of a brown [1±3] betaine ± ylide epimerization [2,3,5] moderated Cl, Br, I, OCH 3 methoxymethoxy-armed ylides [47] no need! (see text) moderated 2-alkenyl methoxymethoxy-armed ylides: present work alkyl P ylides; [38,39] PO ylides [40,41]…”

Section: Resultsmentioning

confidence: 99%

Bridging the Final Gap in Stereocontrolled Wittig Reactions: Methoxymethoxy-Armed Allylic Phosphorus Ylides Affording Conjugated Dienes with Highcis Selectivity

Wang

Khoury

Schlosser³

2000

Chem. Eur. J.

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After treatment with an appropriate base (butyllithium or sodium amide), 2-alkenyltris(2-methoxymethoxyphenyl)phosphonium salts carrying an allyl, crotyl, or prenyl (3-methyl-2-butenyl) side chain condense with saturated or unsaturated aldehydes to give conjugated dienes with Z/E ratios ranging from 90:10 to > 99:1 and averaging 96:4. Owing to steric congestion, yields are only moderate (on average 41%; extremes 10-79%). The nonvolatile tris(2-methoxymethoxyphenyl)phosphine oxide by-product can be readily isolated and reduced to recover the phosphane starting material, or it may be hydrolyzed to the water-soluble tris(2-hydroxyphenyl)phosphine oxide.

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Section: Resultsmentioning

confidence: 99%

Bridging the Final Gap in Stereocontrolled Wittig Reactions: Methoxymethoxy-Armed Allylic Phosphorus Ylides Affording Conjugated Dienes with Highcis Selectivity

Wang

Khoury

Schlosser³

2000

Chem. Eur. J.

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“…The difference of bond angles between sp3 and sp2 hybridized side chains are not more than 10" and are easily compensated by means of conformational processes. Based on these data, all conclusions and interpretations of the biological activities of compounds (3, (6) and (7) are free of sterical influences and can be directly interrelated to their intrinsic I A , 1 0~m electronic properties. Though there is a striking difference in the resulting permanent dipole moment vectors in both types of side chains (in all halogenated derivatives these vectors point towards the more electronegative halogen along the longitudinal axis of the -CHI -Hal moiety), this effect is obviously compensated by means of the unique polarizability of bromine and iodine.…”

Section: Recoginition Of Halogenated 'Multijkienes'mentioning

confidence: 93%

“…Starting from the alcohol (4) [14], the halogen derivatives (9, (6) and (7) were obtained using the halogenating reagents given in Scheme 3 and the references indicated. The two ethers (8) and (9) are accessible by a Williamson-type synthesis [I71 starting from compounds (4) or (6) respectively.…”

Section: Preprution Of a Ttr'uctnntsmentioning

confidence: 99%

“…Comparing the biological activities of the synthetic (f )-multifidene (1) with the halogenated derivatives (5), (6) and (7), it appears that these, otherwise unchanged, molecules are able to imitate the intrinsic properties of the original vinyl group. Parallel to the increasing polarizability of halogenes, the bromo and iodo derivatives are, as expected, the best imitations of the original semiochemical, as may be seen from Table 2 and Fig.…”

Section: Recoginition Of Halogenated 'Multijkienes'mentioning

confidence: 99%

“…The recently examined subclasses Laminariales [ 3 ] and Desmarestiales [4] are oogamous and form semiochemicals which, in addition to attracting sperm, induce the release of sperm from the antheridia. Surprinsingly, such water-borne messengers are strongly hydrophobic: Unsaturated hydrocarbons without other functional groups are the only substances which have been characterized so far [5,6]. Many of them are alicyclic C1l-hydrocarbons with three double bonds, though other degrees of (un)saturation are also well established [7,8].…”

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confidence: 99%

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Binding‐Mechanism and Sensitivity in Gamete Chemotaxis of the Phaeophyte Cutleria multifida

Boland

Terlinden

Jaenicke

et al. 1982

European Journal of Biochemistry

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Female gametes of the marine brown alga Cutleriu multificIa discharge multifidene into the water to attract the swimming males. The physicochemical principle of interaction between semiochemical and membrane receptor site is seen in mutual but complementary induced dipoles. Halogenated derivatives of multifidene with intact overall structure and stereochemistry but altered electronic properties were synthesized and assayed as lures. A direct correlation was observed between increasing polarizability and biological activity, thus proving the proposed mechanism. The low threshold concentration of this communication system (4 x lo9 molecules/ml), together with a detailed knowledge of the gamete's architecture, swimming velocity and stimulus response time, indicates that very few, may be even single, molecules are able to trigger the sensomotoric chain. The rigidity of the natural signal molecule was recognized as an important element in inducing conformational fitting in the ligand/receptor complex.Brown algae (Phaeophyceae) are a cosmopolitan class of the division Heterokontophyta. They have their habitat in the coastal zones of all continents and may grow on rocks, wharves or organic substrates. For reproduction they have evolved a great variety of mechanisms ranging from vegetative propagation to sexual reproduction, including combinations of both. In isogamous and anisogamous forms, flagelbated motile male and female gametes may be released from the respective gametangia. In many cases a secretion of a pheromone is observed after settlement of the female on a surface [ 1,2]. The recently examined subclasses Laminariales [ 3 ] and Desmarestiales [4] are oogamous and form semiochemicals which, in addition to attracting sperm, induce the release of sperm from the antheridia. Surprinsingly, such water-borne messengers are strongly hydrophobic: Unsaturated hydrocarbons without other functional groups are the only substances which have been characterized so far [5,6]. Many of them are alicyclic C1l-hydrocarbons with three double bonds, though other degrees of (un)saturation are also well established [7,8]. Cutleria multifidu, an inhabitant of Mediterranian coastal waters, during spring time releases male and female gametes. After settlement macrogametes secrete a bouquet of three closely related C11H16 substances into the surroundings : multifidene, (+)-(1) ; aucantene, (+)-(2); and ectocarpene, S-( +)-(3). Only the first of them has significant luring activity [9]. The fact that all three compounds belong to the same class of cyclo-olefinic hydrocarbons with similar physicochemical properties but only one of them is the hormone, indicates a very precise messenger/receptor interaction. Receptor studies with about 30 chemically modified 'multifidenes' as parapheromones revealed an unusually low threshold concentration for the natural semiochemical (6.5 pmol/l) and very exacting demands on size and shape [lo]. Partly hydrogenated derivatives of the pheromone underlined the particular importance of the double bonds as ...

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Book Review: Biochemie (Biochemistry). By A. L. Lehninger. Translated by K. Fischer and R. Ries

Cited by 2 publications

References 0 publications

Bridging the Final Gap in Stereocontrolled Wittig Reactions: Methoxymethoxy-Armed Allylic Phosphorus Ylides Affording Conjugated Dienes with Highcis Selectivity

Bridging the Final Gap in Stereocontrolled Wittig Reactions: Methoxymethoxy-Armed Allylic Phosphorus Ylides Affording Conjugated Dienes with Highcis Selectivity

Binding‐Mechanism and Sensitivity in Gamete Chemotaxis of the Phaeophyte Cutleria multifida

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