Thiostrepton. Degradation Products and Structural Features

Bodanszky, Miklos; Fried, Josef; Sheehan, John T.; Williams, Nina J.; Alicino, Joseph F.; Cohen, Allen I.; Keeler, Barbara T.; Birkhimer, Carolyn A.

doi:10.1021/ja01066a035

Cited by 55 publications

(28 citation statements)

References 7 publications

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“…Because of this reaction rare should be taken to avoid contamination of solvents with alcohols during the normal neutralization step. Hydrazine has also proved to be a valuable cleavage method (27,76,228,155) since the resulting peptide hydrazides can be converted to azides for further coupling reactions. Side-chain esters and amides are also reactive and should be avoided during the hydraziriolysis step.…”

Section: Cleavage Methodsmentioning

confidence: 99%

Solid‐Phase Peptide Synthesis

Merrifield¹

1969

Advances in Enzymology - And Related Areas of Molecular Biology

411

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Section: Cleavage Methodsmentioning

confidence: 99%

Solid‐Phase Peptide Synthesis

Merrifield¹

1969

Advances in Enzymology - And Related Areas of Molecular Biology

411

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“…It went rapidly to completion in dimethylformamide, but not in several other solvents. Bodanszky and Sheehan (20) have also found the nitrophenyl esters to be applicable to solid-phase peptide synthesis. Al-though these amino acid derivatives require an additional step in their synthesis, they offer certain compensating advantages.…”

Section: Development Of the Methodsmentioning

confidence: 99%

Automated Synthesis of Peptides

Merrifield

1965

Science

516

255

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essary for self-sufficiency will certainly prevent the attainment of this goal within the foreseeable future. Still, it remains a goal toward which we are moving.Meanwhile, we may expect to see the development of a number of selfsufficient regional calibration centers. With such centers in existence, the national standards laboratories may no longer need to make many calibrations; they can then concentrate more on the development and dissemination of procedures that will permit every major laboratory to reproduce accurately the standard for each quantity. essary for self-sufficiency will certainly prevent the attainment of this goal within the foreseeable future. Still, it remains a goal toward which we are moving.Meanwhile, we may expect to see the development of a number of selfsufficient regional calibration centers. With such centers in existence, the national standards laboratories may no longer need to make many calibrations; they can then concentrate more on the development and dissemination of procedures that will permit every major laboratory to reproduce accurately the standard for each quantity.References and Notes 1. Unfortunately the word standard has multiple meanings in English. In this article the word is used to mean a standard for physical measurement; that is to say, the physical realization of an agreed-upon unit (such as the meter or kilogram) for the expression of physical measurements.References and Notes 1. Unfortunately the word standard has multiple meanings in English. In this article the word is used to mean a standard for physical measurement; that is to say, the physical realization of an agreed-upon unit (such as the meter or kilogram) for the expression of physical measurements.

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“…We then could show for the first time that a three-component system could be prepared that was enzymatically active (62). Thus, RNase (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) plus RNase(21-118) plus RNase(111-124), each containing one of the known catalytic residues of ribonuclease, were mixed noncovalently and found to generate the specific well-ordered structure necessary for substrate binding and catalytic activity.…”

Section: Structure-function Studies On Ribonucleasementioning

confidence: 99%

Solid Phase Synthesis

Merrifield

1986

Science

899

477

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T HE PROTEINS, AS THE GEEK RooToF THEiO NAME implies, are offirst rank in living system, and their smalle relatives, the peptides, have now also been discovered to have importnt roles in biology. Among their m s are many of the hormones, rekasing facrs, growth factors, ion carriers, antibiotics, toxins, and neuropcptides. My purpose tday is to describe the chemical synthesis of peptides and pins dto discuss the useofthe synthcetic approach to answer various biolo l questions. The stry begins with Emil Fisdwr (1) at the tur ofthis century when he synthesized the first peptide and coined the name. The general chemical requirements were to block the arboxyl group of one amino acid and the amino group of the second amino acid.Then, by activatin of the free carboxyl group the peptie bond could be formed, and sclectivc removal ofthe two protecting groups would Icad to the free dipeptide. Fischer himself was never able to find a suitable reversible b ing group for the amine funcion, but his sudent Max Bergmann, t with Leonidas Zervas, was successfl (2). Their design ofthe carbobenzoxy group ushered in a new era. When I began working on the sis of peptides many years later, this same general scheme was universally in use and was very cffective, having led, for example, to the first synthesis of a peptide hormonc by du Vigneaud in 1953 (3). It soon became dar to me, howcevr, that such synteses were difficuk and time consuming, and that a new approach was needed if lar numbes of peptides were required or iflarger and more complex pkptdes were to be made. Synthesis on a Solid MatrixOne day I had an idea about how the goal of a morc efficent synthesis might be achieved. Thc plan (4) was to assemble a pcptidc chain in a stepwise manner while it was a A atone end to a solid support. With the growing chain covaently anchored to an insolublc matrix at all stages of the synthsis, the peptidc would also bc compktely insoluble and, fiurhermore, would be in a suitable physical form to permit rapid filtration and washing after completion of each ofthe synetic reactions. be in it pepds in the synthesis would thus be purified by a vcry simple, rapid prcedure rather than by the usual tedious ystizai me s. When a mutistep process, such as the p on of a long polyeptide or protein, is contemplated the saving in time, effort, and materials could be very large. Thc fact that all of the stps jt described are hetcrogeneous reactions between a solubk reagent in the liquid phase and the growing peptid chain in the insoluble solid phase led to the introduction of the name "solid phase peptid synthesis."The general scheme for solid phase synthesis is oudined in Fig. 1. It begins with an insolublc particle (large crcles), which is functioalized with a group, X. The first monomer unit (sml crcles) is blockd at one end and at the reactve side-chain groups (black dots) and anchored to the support by a stable covalent bond. The a prtcting group is then renoved and the second monomer unit is added to the first by a suitable reaction. In a similar way th...

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Thiostrepton. Degradation Products and Structural Features

Cited by 55 publications

References 7 publications

Solid‐Phase Peptide Synthesis

Solid‐Phase Peptide Synthesis

Automated Synthesis of Peptides

Solid Phase Synthesis

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