Biological molecules

Common protection methods for N-terminus of an amino acid (general) (2)

Boc (Boc2O) + base, Fmoc-Cl + base

How to deprotect Boc

TFA F3C-COOH

How to deprotect Fmoc

piperidine

Common protecting groups of the carboxylic acid of the C-terminus (general) (4)

generally esterification with an alcohol (MeOH + HCl(methyl ester)/ Bn-COH+ HCl(benzyl ester)/ allyl ester/ tert-butyl ester)

How to deprotect the methyl ester

NaOH, H2O

how to deprotect the benzyl ester/ether

H2/ Pd/C

how to deprotect the allyl ester

Pd(PPh3)4

how to deprotect tert-butyl ester/ether?

TFA

common methods to protect hydroxyl groups (3)

tert-butyl ether, benzyl ether, silyl ether

How to deprotect a silyl ether

TBAF

Whats the issue with activating the C-terminus as an acid chloride

racemisation of the activated amino acid forming unwanted byproducts with the wrong stereochemistry caused by oxazolone formation

what do we use to activate the C- terminus and examples (2)

coupling reagent, DCC and HATU +base

How to selectively protect the anomeric OH

MeOH + HCl

How to selectively deprotect the anomeric OH?

H2NNH2 or benzyl amine

How to selectively protect the 1,3-diols?

Benzylidene acetal + acid

How to selectively deprotect the C4-OH

NaBH4

How to selectively deprotect the C6-OH

LiAlH4