Notes in BioOrganic -- Harding Section

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Published	10/29/2024	What does the L in L-alanine represent?
Published	10/29/2024	What does the α in L-α-alanine represent?
Published	10/29/2024	Amino acids exist as {{c1::dipolar ions (zwitterions}}. The predominant form depends on the {{c2::pH of the solution}}
Published	10/29/2024	What determines the predominant form of amino acids in solution?
Published	10/29/2024	{{c1::image-occlusion:rect:left=.4174:top=.4713:width=.1857:height=.1265:oi=1}}{{c2::image-occlusion:rect:left=.7317:top=.4832:width=.2544:height=.502…
Published	10/29/2024	What amino acid form predominates in acidic solutions?
Published	10/29/2024	What amino acid form predominates in strongly basic solutions?
Published	10/29/2024	What is the net charge of a zwitterion?
Published	10/29/2024	At {{c1::low}} pH the amino acid exists primarily in the {{c2::cationic}} form
Published	10/29/2024	At {{c1::high}} pH the amino acid exists primarily in the {{c2::anionic}} form
Published	10/29/2024	At the {{c1::isoelectric point, pI}}, the concentration of the {{c2::dipolar ion}} is at a {{c3::maximum}} and the concentrations of th…
Published	11/05/2024	Why is the pKa1 of alanine much lower than propanoic acid?
Published	11/05/2024	How do you calculate the isoelectric point of a neutral amino acid, such as alanine?
Published	11/05/2024	When base is slowly added to fully protonated alanine, a pH is reached where {{c1::half}} the {{c2::carboxylic acid}} groups are deprotonate…
Published	11/05/2024	Is the isoelectric point of lysine higher, lower, or similar to alanine? Why?
Published	11/05/2024	How do you calculate the isolectric point of acidic amino acids?
Published	11/05/2024	How do you calculate the isoelectric point of basic amino acids?
Published	11/05/2024	Draw the 4 ionic forms of lysine as it is titrated with base (pH=2 ~12)
Published	11/05/2024	What is the purpose of synthesizing amino acids?
Published	11/05/2024	Natural amino acids can be synthesized by {{c1::fermentation}}
Published	11/05/2024	What are the 5 methods of racemic amino acid synthesis?
Published	11/05/2024	What are the two methods to synthesize chiral amino acids?
Published	11/05/2024	Which reaction is this?
Published	11/05/2024	{{c1::image-occlusion:rect:left=.2627:top=.3233:width=.1278:height=.1504:oi=1}}{{c2::image-occlusion:rect:left=.6055:top=.2706:width=.1116:height=.180…
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Published	11/05/2024	Draw the HVZ synthesis for valine.
New Card	11/06/2024	What is the first step of HVZ synthesis?
New Card	11/06/2024	What group leaves in the first step of HVZ? What group is added?
New Card	11/06/2024	Why is excess NH3 used in HVZ?
New Card	11/06/2024	What is a con of HVZ synthesis?
New Card	11/06/2024	What reaction is this?
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New Card	11/06/2024	What molecule do you begin with in amidomalonate synthesis?
New Card	11/06/2024	What is the first step of amidomalonate synthesis?
New Card	11/06/2024	What is the second step of aminodmalonate synthesis?
New Card	11/06/2024	What is the intermediate structure of amidomalonate synthesis?
New Card	11/06/2024	Draw the structure of diethyl acetamidomalonate
New Card	11/06/2024	What is the final step of amidomalonate synthesis?
New Card	11/06/2024	What are the limitations of amidomalonate synthesis?
New Card	11/06/2024	Which R groups are compatible with amidomalonate synthesis?
New Card	11/06/2024	Which R groups are incompatible with amidomalonate synthesis?
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	What is the source of nitrogen in Gabriel synthesis?
New Card	11/06/2024	What is the first step of Gabriel synthesis?
New Card	11/06/2024	Draw the structure of phtalimide
New Card	11/06/2024	What is the second step of Gabriel synthesis?
New Card	11/06/2024	Why is the proton in pthalimide acidic?
New Card	11/06/2024	What is the final step(s) of Gabriel synthesis?
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	What are the starting reagents of malonic ester variant Gabriel synthesis?
New Card	11/06/2024	What is the first step of malonic ester variant Gabriel synthesis?
New Card	11/06/2024	What is the second step of malonic ester variant of Gabriel synthesis?
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	What is the starting substrate in Strecker synthesis?
New Card	11/06/2024	What is the first step of Strecker synthesis?
New Card	11/06/2024	What is the source of ammonia in Strecker synthesis?
New Card	11/06/2024	What is the intermediate of Strecker synthesis?
New Card	11/06/2024	What is the second step of Strecker synthesis?
New Card	11/06/2024	{{c1::Strecker}} synthesis is a {{c2::multicomponent}} reaction, as it is comprised of more than 2 reactants
New Card	11/06/2024	{{c1::Strecker}} synthesis proceeds via the {{c2::iminium}} ion
New Card	11/06/2024	{{c1::image-occlusion:rect:left=.1716:top=.3053:width=.1812:height=.1275:oi=1}}{{c2::image-occlusion:rect:left=.6228:top=.2382:width=.0871:height=.174…
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New Card	11/06/2024	What mechanism is this?
New Card	11/06/2024	Reduction of an {{c1::alpha-keto acid}} with {{c2::NH3}} and a {{c3::reducing agent}} produces an {{c4::alpha-amino acid}}
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	What is the process of reductive amination?
New Card	11/06/2024	Why is ammonia added before NaBH4 in reductive amination?
New Card	11/06/2024	What reducing agents can be used in place of NaBH4 in reductive amination? What is the benefit of these reagents?
New Card	11/06/2024	What is the adavantage of asymmetric synthesis?
New Card	11/06/2024	How can you measure the success of asymmetric synthesis?
New Card	11/06/2024	How do you calculate enatiomeric excess?
New Card	11/06/2024	An enantioselective reaction gives two products A and B where the enantiomeric excess (ee) of compound A is 90%. What is the percentage composition of…
New Card	11/06/2024	What are the two methods for asymmetric synthesis?
New Card	11/06/2024	If you start with an (S)-substrate, what is the configuration of the product in asymmetric synthesis?
New Card	11/06/2024	What is the first step of asymmetric synthesis by use of chiral substrate?
New Card	11/06/2024	What is the second step of asymmetric synthesis using a chiral substrate?
New Card	11/06/2024	Why is the product of asymmetric synthesis with a chiral substrate inverted?
New Card	11/06/2024	How does asymmetric synthesis via a chiral catalyst proceed?
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	{{c1::image-occlusion:rect:left=.6676:top=.2388:width=.0838:height=.0755:oi=1}}
New Card	11/06/2024	{{c1::image-occlusion:rect:left=.6657:top=.3521:width=.0585:height=.0566:oi=1}}
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	{{c1::image-occlusion:rect:left=.2505:top=.1495:width=.0838:height=.1904:oi=1}}{{c2::image-occlusion:rect:left=.2583:top=.5563:width=.0624:height=.147…
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New Card	11/06/2024	What is the purpose of a chiral auxillary group?
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	How does use of a chiral auxillary group induce chirality in the product?
New Card	11/06/2024	What reaction is this?
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New Card	11/06/2024	What is the general mechanism of chiral resolution?
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	What is the first step of chiral resolution?
New Card	11/06/2024	What is the second step of chiral resolution?
New Card	11/06/2024	How do you seperate the diastereomers during chiral resolution?
New Card	11/06/2024	How is the chosen diastereomer converted to an amino acid during chiral resolution?
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New Card	11/06/2024	What are the 3 main groups used in peptide synthesis?
New Card	11/06/2024	What are the main two types of protecting groups?
New Card	11/06/2024	What are the main 2 types of activating groups?
New Card	11/06/2024	{{c1::Peptide bonds}} are formed by a {{c2::condensation reaction}} of {{c3::carboxylic group}} of an amino acid and an {{c4::amino gro…
New Card	11/06/2024	What reaction forms peptide bonds?
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	What are the 2 general approaches to peptide synthesis?
New Card	11/06/2024	When are coupling agents required in peptide synthesis?
New Card	11/06/2024	What is the risk of use an amide protecting group for peptide synthesis?
New Card	11/06/2024	What group does BOC protect?
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New Card	11/06/2024	How are BOC groups removed?
New Card	11/06/2024	With which amino acids should the use of Boc be avoided? Why?
New Card	11/06/2024	How is a hydrazone linkage formed?
New Card	11/06/2024	{{c1::image-occlusion:rect:left=.2725:top=.611:width=.1429:height=.1156:oi=1}}{{c2::image-occlusion:rect:left=.7046:top=.6341:width=.1464:height=.0971…
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New Card	11/06/2024	What is the structure of hydrazine?
New Card	11/06/2024	What is the structure of hydrazone?
New Card	11/06/2024	How does oxime ligation occur?
New Card	11/06/2024	What type of ligation is this?
New Card	11/06/2024	{{c1::image-occlusion:rect:left=.0485:top=.7175:width=.1464:height=.1367:oi=1}}{{c2::image-occlusion:rect:left=.7593:top=.7237:width=.1058:height=.136…
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New Card	11/06/2024	What type of ligation is this?
New Card	11/06/2024	How can you accelerate oxime ligation?
New Card	11/06/2024	What reaction is this?
New Card	11/06/2024	What is the role of aniline in oxime ligation?
New Card	11/06/2024	Why is oxime ligation more favorable than hydrazone?
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New Card	11/06/2024	What type of ligation is this?
New Card	11/06/2024	What are the advantages of thiazolidine ligation?
New Card	11/06/2024	What are the disadvantages of thiazolidine ligation?
New Card	11/06/2024	What type of ligation is this?
New Card	11/10/2024	What is a limitation of SPPS?
New Card	11/10/2024	Why is the length of peptide chains created using SPPS limited?
New Card	11/10/2024	Who developed SPPS?
New Card	11/10/2024	{{c1::Native chemical ligation}} allows for the construction og longer peptide chains while retaining the native {{c2::peptide backbone}}, which …
New Card	11/10/2024	The basis of {{c1::NCL}} allows for the coupling of {{c2::two individual fully deprotected peptide fragments}} in an aqueous solution to for…
New Card	11/10/2024	What is the basic premise of NCL?
New Card	11/10/2024	NCL in conjugation with {{c1::SPPS}} can be used to make functional proteins that are {{c2::~250 amino acids in length}}
New Card	11/10/2024	One of the earliest forms of ligation utilized a {{c1::hydrazone}} linkage, an {{c2::amine derivative}} of an {{c3::imine}}
New Card	11/10/2024	How does hydrazone ligation proceed?
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New Card	11/10/2024	Draw a basic hydrazone ligation.
New Card	11/10/2024	What is a drawback of hydrazone ligation?
New Card	11/10/2024	How can hydrazone ligations be sped up?
New Card	11/10/2024	What are the advantages of hydrazone ligation?
New Card	11/10/2024	What are the conditions for hydrazone ligation?
New Card	11/10/2024	What are the conditions for oxime ligation?
New Card	11/10/2024	How does aniliine speed up oxime formation?
New Card	11/10/2024	How can you speed up oxime formation?
New Card	11/10/2024	How can you reduce the number of side reactions in oxime ligation?
New Card	11/10/2024	What is the advantage of oxime formation compared to hydrazone?
New Card	11/10/2024	What type of ligation is this? What is the final product?
New Card	11/10/2024	What type of ligation is this?
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New Card	11/10/2024	What are the advantages of oxime ligation?
New Card	11/10/2024	What are the disadvantages of oxime ligation?
Published	11/10/2024	What type of ligation is this?
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New Card	11/10/2024	What are the disadvantages of thiazolidine ligation?
New Card	11/10/2024	What are the advantages of thiazolidine ligation?
Published	11/10/2024	What is the mechanism of thioester ligation?
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