Total Syntheses of Nα- [1-(2-Acetamido-3-O-D-glucosyl)-D-propionyl-L-alanyl-D-α- and γ-glutamyl]-L-lysyl-D-alanyl-D-alanine, and Identity of the γ-Glutamyl Isomer with the Glycopeptide of a Bacterial Cell Wall Precursor

Lanzilotti, A. E.; Benz, Edward J.; Goldman, Lenka

doi:10.1021/ja01063a064

Cited by 23 publications

(5 citation statements)

References 15 publications

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“…It has been demonstrated by hydrazinolysis (Ito and Strominger, 1964) and synthetic studies (Lanzillotti et al, 1964) that in this precursor the 7-carboxyl of D-glutamic acid is linked to the -amino group of L-lysine. The -carboxyl group of glutamic acid in this precursor is unsubstituted.…”

mentioning

confidence: 99%

Substituents on the α-Carboxyl Group of D-Glutamic Acid in the Peptidoglycan of Several Bacterial Cell Walls^*

Tipper¹,

Katz²,

Strominger³

et al. 1967

Biochemistry

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confidence: 99%

Substituents on the α-Carboxyl Group of D-Glutamic Acid in the Peptidoglycan of Several Bacterial Cell Walls^*

Tipper¹,

Katz²,

Strominger³

et al. 1967

Biochemistry

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“…The zone with R¡ 0.34 yielded a syrup which crystallized after the same procedure (above) was applied to the main reaction mixture syrup. In several preparative chromatographic runs the few milligrams of product isolated from the zone with R¡ 0.34 were identical with that crystallized above: mp 176°; [a]25d -37.6°(c 0.77, chloroform); X*®' 3.00 (N-H), 3.40 (C-H), 5.70 (-C02CH3, -OAc), 6.02 (amide I), 6.15 (Ar-), 6.30 (-NOs), 6.55 (amide II), 6.62 (-N02), 7.00, 7.30, 7.48 (-N02), 8.15, 9.50, 10.20, 10.80, 13.40…”

mentioning

confidence: 59%

“…Coupling constant, J, in cycles per second. 6 Obscured by CH2D-and -OCIl3 signals. As correlated with ref 27, these are in the H-2' and 11-5' region.…”

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confidence: 99%

“…Water was added to the yellow ethanol solution until turbidity appeared and the mixture was warmed until clear again. Cooling of the solution in a warmwater bath at the rate of bath equilibrium with room temperature (3 hr) gave crystals, which were filtered, washed with ether, and dried: yield, 6.8 g (69%); mp99°; [cel^D -26°(c 0.77, chloroform); X™' 2.81 (OH), 2.93 (N-H), 3.50 (C-H), 5.70 (-CO2CH3), 6.15, 6.28 (Ar), 6.55, 6.65 (-N02), 7.00, 7.35 (N02),…”

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confidence: 99%

“…A fast-moving yellow zone was first eluted from the column. Removal of chromatography solvent from this first fraction, solution of the syrup in warm ethanol, and filtration, on cooling, permitted crystallization of orange needles: 0.015 g. (20.2%); mp 67-70°; [ ]25 0.00 (c 0.2, HCCh); 3.00 (N-H), 5.75 (-C02CH3), 6.15 (H2-C=C<), 6.28 (Ar-), 6.60 (N02), 6.91, 7.50, 8.20, 9.90, 10.48 (R>C=CH2), 10.80, 12.43, 13.50 µ. Nmr spectroscopy data are recorded in Table I. The compound was chromatographically homogeneous in solvents A, B, and C: fif 0.95 (solvent A, silica gel G33).…”

mentioning

confidence: 99%

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β Elimination of Glycoside Monosaccharide from a 3-O-(2-Amino-2-deoxy-D-glucopyranosyl)serine. Evidence for an Intermediate in Glycoprotein Hydrolysis¹

Vercellotti¹,

Luetzow²

1966

J. Org. Chem.

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The p elimination of glycoside carbohydrate from p-hydroxy amino acids during glycoprotein hydrolysis in basic media to produce a,p-unsaturated amino acid derivatives as reactive intermediates is verified with a modelmethyl ester, which was syntheaized and definitively characterized. Simulation of a possible enzymesubstrate intermediate with decreased electron density on the amino acid nitrogen was effected by conducting base-catalyzed hydrolysis on the above N-2,4-dinitrophenylserine derivative. I n dilute base under a variety of experimental conditions, elimination of the hexosamine intact and formation of N-2,4-dinitrophenyla-aminoacrylic acid occurred. The latter compound was isolated crystalline in 20% yield from the basic hydrolytic medium and its identity was affirmed by nmr spectroscopy.

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Hormon‐Rezeptor‐Wechselwirkungen. Synthese von α‐Melanotropin und von informationstragenden Teilsequenzen unter Verwendung alkalilabiler Schutzgruppen

Eberlé¹,

Fauchère²,

Tesser³

et al. 1975

Helvetica Chimica Acta

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Sequences thereof with the Aid of Alcali-Labile Protectiirg Groups. Summary. Thc aim of this investigation waa to prepare a-melanotropin and partial sequences thereof for biological investigatians in as pure a state as possible. Classical synthesis in solution was chosen an the general approach. because it allows for extcnsive purification and identiiication of all intermediates, thus warranting thc chemical idcntity of the products (in contrast to the solidphase methods). The scheme of protection was its follows: for the Na-amino groups mostly f-butoxycarbonyl (BOG), sometimes bcnzyloxycarbonyl (2-), for the Ne-amino group ot lysine-(11) 2-(rnethylsulfony1)-ethaxycarbonyl (MSOC-), and for the carboxylic acid group of Ctcrminal glycine-(10) 2-(4-tolylsulfony1)-cthoxy (-OTSE). This provides for facile and mild selecfive deprotection of either the aamp0 grdups by acidolysis or of the 6-amino group (a-carboxyl group) byp-elimination in alcali. A slight molar oxass of 0 . 1 2~ HCI in HCOOK proved to be the mctbod of choice for removing BOG; MSOC-is stable in acid (even for 30 min in liquid HF) and easily removed in a few minutcs by 0.05-0.1~ Ba(0H)e ; -OTSE is removed similarly. Condensation of amino-acid and peptide dorivatives (formation of the peptide link) was performed using active csters (-ONP; -OSU), dicyclohexylcarbodiimide (DCCI) with or without 1-hydroxy-benzotriazole (HDBT), or carboxylic acid azides wherever histidinc was the carboxylic component.More than 50 compounds are described. Thosc characterized by arabic numerals servcd to prove that a-MSH contains two message sequences that are able to trigger melanocytc responsc : one in the central region -His-Phe-Arg-Trp-, thc other in the C-terminal portion -Gly-Lys-~o-vzdl* NHs of the molecule [3].Einlelltung.

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Total Syntheses of N^α- [1-(2-Acetamido-3-O-D-glucosyl)-D-propionyl-L-alanyl-D-α- and γ-glutamyl]-L-lysyl-D-alanyl-D-alanine, and Identity of the γ-Glutamyl Isomer with the Glycopeptide of a Bacterial Cell Wall Precursor

Cited by 23 publications

References 15 publications

Substituents on the α-Carboxyl Group of D-Glutamic Acid in the Peptidoglycan of Several Bacterial Cell Walls^*

Substituents on the α-Carboxyl Group of D-Glutamic Acid in the Peptidoglycan of Several Bacterial Cell Walls^*

β Elimination of Glycoside Monosaccharide from a 3-O-(2-Amino-2-deoxy-D-glucopyranosyl)serine. Evidence for an Intermediate in Glycoprotein Hydrolysis¹

Hormon‐Rezeptor‐Wechselwirkungen. Synthese von α‐Melanotropin und von informationstragenden Teilsequenzen unter Verwendung alkalilabiler Schutzgruppen

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Total Syntheses of Nα- [1-(2-Acetamido-3-O-D-glucosyl)-D-propionyl-L-alanyl-D-α- and γ-glutamyl]-L-lysyl-D-alanyl-D-alanine, and Identity of the γ-Glutamyl Isomer with the Glycopeptide of a Bacterial Cell Wall Precursor

Cited by 23 publications

References 15 publications

Substituents on the α-Carboxyl Group of D-Glutamic Acid in the Peptidoglycan of Several Bacterial Cell Walls*

Substituents on the α-Carboxyl Group of D-Glutamic Acid in the Peptidoglycan of Several Bacterial Cell Walls*

β Elimination of Glycoside Monosaccharide from a 3-O-(2-Amino-2-deoxy-D-glucopyranosyl)serine. Evidence for an Intermediate in Glycoprotein Hydrolysis1

Hormon‐Rezeptor‐Wechselwirkungen. Synthese von α‐Melanotropin und von informationstragenden Teilsequenzen unter Verwendung alkalilabiler Schutzgruppen

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Total Syntheses of N^α- [1-(2-Acetamido-3-O-D-glucosyl)-D-propionyl-L-alanyl-D-α- and γ-glutamyl]-L-lysyl-D-alanyl-D-alanine, and Identity of the γ-Glutamyl Isomer with the Glycopeptide of a Bacterial Cell Wall Precursor

Substituents on the α-Carboxyl Group of D-Glutamic Acid in the Peptidoglycan of Several Bacterial Cell Walls^*

Substituents on the α-Carboxyl Group of D-Glutamic Acid in the Peptidoglycan of Several Bacterial Cell Walls^*

β Elimination of Glycoside Monosaccharide from a 3-O-(2-Amino-2-deoxy-D-glucopyranosyl)serine. Evidence for an Intermediate in Glycoprotein Hydrolysis¹